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Information on EC 2.5.1.31 - ditrans,polycis-undecaprenyl-diphosphate synthase [(2E,6E)-farnesyl-diphosphate specific]
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2.5.1.31 ditrans,polycis-undecaprenyl-diphosphate synthase [(2E,6E)-farnesyl-diphosphate specific]IUBMB Comments
Undecaprenyl pyrophosphate synthase catalyses the consecutive condensation reactions of a farnesyl diphosphate with eight isopentenyl diphosphates, in which new cis-double bonds are formed, to generate undecaprenyl diphosphate that serves as a lipid carrier for peptidoglycan synthesis of bacterial cell wall .
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Word Map
- 2.5.1.31
- cis-prenyltransferase
-
isoprenoids
- prenyltransferases
- dolichols
- luteus
- dhdds
- trans-prenyltransferases
- pharmacology
-
octaprenyl
- medicine
- drug development
The expected taxonomic range for this enzyme is: Bacteria, Archaea, Eukaryota
Reaction Schemes
Synonyms
bactoprenyl-diphosphate synthase, C55-OO synthetase, C55PP synthetase, cis,polyprenyl diphosphate synthase, cis-prenyl chain elongating enzyme, cis-type undecaprenyl pyrophosphate synthase, CPDS, DDPPs, dehydrodolichyl diphosphate synthase, di-trans,poly-cis-decaprenylcistransferase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
bactoprenyl-diphosphate synthase
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C55-OO synthetase
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C55PP synthetase
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cis,polyprenyl diphosphate synthase
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cis-prenyl chain elongating enzyme
CPDS
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DDPPs
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dehydrodolichyl diphosphate synthase
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-
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di-trans,poly-cis-decaprenylcistransferase
di-trans,poly-cis-undecaprenyl-diphosphate synthase
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di-trans-poly-cis-decaprenyl cistransferase
synthetase, undecaprenyl pyrophosphate
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undecaprenyl diphosphate synthase
undecaprenyl diphosphate synthetase
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undecaprenyl pyrophosphate synthase
undecaprenyl pyrophosphate synthetase
undecaprenyl-diphosphate synthase
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UPP synthase
UPP synthetase
UPP, C55 synthase
UPPs
UPS
Z-prenyl diphosphate synthase
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-
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additional information
undecaprenyl diphosphate synthase
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undecaprenyl diphosphate synthase
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undecaprenyl pyrophosphate synthase
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undecaprenyl pyrophosphate synthetase
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UPP synthetase
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UPPs
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UPPs
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UPS
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
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-
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(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
active site structure and catalytic mechanism
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(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
active site structure, detailed catalytic mechanism, substrate binding mechanism, D26, H43, S71, N74, and R77 are involved
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
substrate binding mode and catalytic mechanism involving active site residue Asp26 which serves as general base, overview
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(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
catalytic mechanism, overview
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(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
catalytic mechanism, overview
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(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
catalytic mechanism, overview
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
ditrans,octacis-undecaprenyl diphosphate substrate binding mode and catalytic mechanism involving active site residue Asp26 which serves as general base, overview
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(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
catalytic mechanism, overview
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
alkenyl group transfer
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PATHWAY SOURCE
PATHWAYS
BRENDA
KEGG
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SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl-diphosphate:isopentenyl-diphosphate cistransferase (adding 8 isopentenyl units)
Undecaprenyl pyrophosphate synthase catalyses the consecutive condensation reactions of a farnesyl diphosphate with eight isopentenyl diphosphates, in which new cis-double bonds are formed, to generate undecaprenyl diphosphate that serves as a lipid carrier for peptidoglycan synthesis of bacterial cell wall [3].
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CAS REGISTRY NUMBER
COMMENTARY
52350-87-5
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2E,6E)-8-(N-methyl-2-aminobenzoyloxy)-3,7-dimethyl-2,6-octandien-1-diphosphate + 8 isopentenyl diphosphate
?
-
a fluorescent analog of farnesyl diphosphate
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
(2E,6E)-farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans,poly-cis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + isopentenyl diphosphate
diphosphate + ditrans,polycis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl thiodiphosphate + isopentenyl diphosphate
?
-
weak activity, 10000000fold lower than with (2E,6E)-farnesyl diphosphate
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-
?
(2Z,6E,10E,14E)-farnesylgeranyl diphosphate + isopentenyl diphosphate
?
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-
-
-
?
(2Z,6Z,10E,14E)-farnesylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
-
?
(E)-3-methyl-3-pentenyl diphosphate + isopentenyl diphosphate
?
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reactive as substrate and competitive inhibition profile
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-
?
2-nitrileanilinogeranyl diphosphate + 9 isopentenyl diphosphate
9 diphosphate + 2-nitrileanilinobactoprenyl diphosphate
7-(2,6-dimethyl-8-diphospho-2,6-octadienyloxy)-8-methyl-4-trifluoromethyl-chromen-2-one geranyl diphosphate + isopentenyl diphosphate
?
-
fluorescent analogue of (2E,6E)-farnesyl diphosphate, alternative substrate and inhibitor
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-
?
di-trans-poly-cis-decaprenyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + undecaprenyl diphosphate
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neither dimethylallyl diphosphate nor geranyl diphosphate act as priming substrate for the enzyme
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-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
farnesyl phosphate + isopentenyl diphosphate
phosphate + di-trans-poly-cis-undecaprenyl diphosphate
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low activity
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?
geranyl diphosphate + isopentenyl diphosphate
?
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C10 GPP displays a 90fold larger Km value compared with (2E,6E)-farnesyl diphosphate
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?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + ?
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less effective than farnesyl diphosphate
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?
geranylgeranyl diphosphate + isopentenyl diphosphate
?
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containing a larger C20 hydrocarbon tail, is an equally good substrate
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?
geranylgeranyl diphosphate + isopentenyl diphosphate
diphosphate + ?
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as effective as farnesyl diphosphate
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?
isopentenyl diphosphate + (E,E)-(2-diazo-3-trifluoropropionyloxy)geranyl diphosphate
(E,E)-(2-diazo-3-trifluoropropionyloxy)polyprenyl diphosphate + diphosphate
isopentenyl diphosphate + dimethylallyl diphosphate
?
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2% of the activity with farnesyl diphosphate
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-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
isopentenyl diphosphate + geranyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
isopentenyl diphosphate + geranylgeranyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
isopentenyl diphosphate + geranylneryl diphosphate
?
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cis,trans,trans-geranylneryl diphosphate
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-
?
isopentenyl diphosphate + neryl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
isopentenyl diphosphate + S-farnesyl thiodiphosphate
?
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weak activity, 10000000fold lower than with farnesyl diphosphate
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-
?
N-(4-benzoylphenyl)-4-hydroxy-2-oxo-5-phenethyl-2,5-dihydro-1H-pyrrole-3-carboxamide + isopentenyl diphosphate
?
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Photo-probe
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-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
the enzyme catalyzes the synthesis of the C55 lipid undecaprenyl diphosphate through eight consecutive condensations of isopentenyl pyrophosphate
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
the enzyme catalyzes the synthesis of the C55 lipid undecaprenyl diphosphate through eight consecutive condensations of isopentenyl pyrophosphate
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
quantification of product distribution of UPPs catalyzed coupling of (2E,6E)-farnesyl diphosphate and isopentenyl diphosphate under various reaction conditions
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
catalyzes the condensation of eight molecules of isopentenyl pyrophosphate (IPP) with farnesyl diphosphate (FPP) to generate C55 undecaprenyl diphosphate. With a variety of different ratios of enzyme to substrate and FPP to IPP in the presence or absence of Triton, different product distributions are found
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
UPPS catalyzes eight consecutive condensation steps of IPP with FPP to form C55 final product
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
the enzyme is responsible for the biogenesis of undecaprenyl phosphate, an indispensable glycosyl carrier lipid in bacterial cell wall biosynthesis
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
the enzyme catalyzes the synthesis of the C55 lipid undecaprenyl diphosphate through eight consecutive condensations of isopentenyl pyrophosphate
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
the enzyme is responsible for the biogenesis of undecaprenyl phosphate, an indispensable glycosyl carrier lipid in bacterial cell wall biosynthesis
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
the enzyme catalyzes the synthesis of the C55 lipid undecaprenyl diphosphate through eight consecutive condensations of isopentenyl pyrophosphate
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
trans,trans-farnesyl diphosphate
C55 polyprenyl diphosphate with isoprene residues with cis stereochemistry
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
catalyzes the cis-prenyl chain elongation onto trans,trans-farnesyl diphosphate (FPP) to produce undecaprenyl diphosphate (UPP). The product undecaprenyl diphosphate is indispensable for the biosynthesis of bacterial cell walls
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
catalyzes the sequential condensation of eight molecules of isopentenyl diphosphate (IPP) in the cis-configuration into farnesyl diphosphate (FPP) to produce undecaprenyl diphosphate (UPP), which is indispensable for the biosynthesis of the bacterial cell wall
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
catalyzes the cis-prenyl chain elongation onto trans,trans-farnesyl diphosphate (FPP) to produce undecaprenyl diphosphate (UPP). The product undecaprenyl diphosphate is indispensable for the biosynthesis of bacterial cell walls
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
catalyzes the sequential condensation of eight molecules of isopentenyl diphosphate (IPP) in the cis-configuration into farnesyl diphosphate (FPP) to produce undecaprenyl diphosphate (UPP), which is indispensable for the biosynthesis of the bacterial cell wall
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
the enzyme catalyzes the synthesis of the C55 lipid undecaprenyl diphosphate through eight consecutive condensations of isopentenyl pyrophosphate
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
the enzyme catalyzes the synthesis of the C55 lipid undecaprenyl diphosphate through eight consecutive condensations of isopentenyl pyrophosphate
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E,10E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
-
?
(2E,6E,10E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
?
(2E,6E,10E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
?
(2Z,6E,10E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
-
?
(2Z,6E,10E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
-
?
(2Z,6E,10E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
?
(2Z,6E,10E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
?
(2Z,6E,10E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
-
?
(2Z,6E,10E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
?
(2Z,6E,10E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
-
?
(2Z,6E,10E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
?
(Z,E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
-
?
2-amideanilinogeranyl diphosphate + isopentenyl diphosphate
?
lower activity, the fluorescent substrate analogue undergoes a 1.2fold increase in fluorescence upon isoprenoid chain elongation, and this increase in fluorescence can be utilized to monitor the activity and inhibition of UPPS in 96-well plate assays
ESI-MS analysis suggests that these major product peaks correspond to six to nine Z-configuration isoprenes incorporated by the UPPS protein
-
?
2-amideanilinogeranyl diphosphate + isopentenyl diphosphate
?
lower activity, the fluorescent substrate analogue undergoes a 1.2fold increase in fluorescence upon isoprenoid chain elongation, and this increase in fluorescence can be utilized to monitor the activity and inhibition of UPPS in 96-well plate assays
ESI-MS analysis suggests that these major product peaks correspond to six to nine Z-configuration isoprenes incorporated by the UPPS protein
-
?
2-nitrileanilinogeranyl diphosphate + 9 isopentenyl diphosphate
9 diphosphate + 2-nitrileanilinobactoprenyl diphosphate
the fluorescent substrate analogue undergoes a 2.5fold increase in fluorescence upon isoprenoid chain elongation, and this increase in fluorescence can be utilized to monitor the activity and inhibition of UPPS in 96-well plate assays
-
-
?
2-nitrileanilinogeranyl diphosphate + 9 isopentenyl diphosphate
9 diphosphate + 2-nitrileanilinobactoprenyl diphosphate
the fluorescent substrate analogue undergoes a 2.5fold increase in fluorescence upon isoprenoid chain elongation, and this increase in fluorescence can be utilized to monitor the activity and inhibition of UPPS in 96-well plate assays
-
-
?
2-nitrileanilinogeranyl diphosphate + 9 isopentenyl diphosphate
9 diphosphate + 2-nitrileanilinobactoprenyl diphosphate
the fluorescent substrate analogue undergoes a 2.5fold increase in fluorescence upon isoprenoid chain elongation, and this increase in fluorescence can be utilized to monitor the activity and inhibition of UPPS in 96-well plate assays
-
-
?
2-nitrileanilinogeranyl diphosphate + 9 isopentenyl diphosphate
9 diphosphate + 2-nitrileanilinobactoprenyl diphosphate
the fluorescent substrate analogue undergoes a 2.5fold increase in fluorescence upon isoprenoid chain elongation, and this increase in fluorescence can be utilized to monitor the activity and inhibition of UPPS in 96-well plate assays
-
-
?
2-nitrileanilinogeranyl diphosphate + 9 isopentenyl diphosphate
9 diphosphate + 2-nitrileanilinobactoprenyl diphosphate
the fluorescent substrate analogue undergoes a 2.5fold increase in fluorescence upon isoprenoid chain elongation, and this increase in fluorescence can be utilized to monitor the activity and inhibition of UPPS in 96-well plate assays
-
-
?
2-nitrileanilinogeranyl diphosphate + 9 isopentenyl diphosphate
9 diphosphate + 2-nitrileanilinobactoprenyl diphosphate
the fluorescent substrate analogue undergoes a 2.5fold increase in fluorescence upon isoprenoid chain elongation, and this increase in fluorescence can be utilized to monitor the activity and inhibition of UPPS in 96-well plate assays
-
-
?
di-trans-poly-cis-decaprenyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
-
di-trans-poly-cis-decaprenyl diphosphate is farnesyl diphosphate
-
-
?
di-trans-poly-cis-decaprenyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
-
di-trans-poly-cis-decaprenyl diphosphate is farnesyl diphosphate, the diphosphate head group of farnesyl diphosphate is bound to the backbone of NHs pf G29 and R30 as well as the side chains of N28, R30, and R39 through hydrogen bonds, H43 may stabilize the farnesyl cation intermediate during catalysis being near to the C2 carbon of farnesyl diphosphate
-
-
?
di-trans-poly-cis-decaprenyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
di-trans-poly-cis-decaprenyl diphosphate is farnesyl diphosphate, isopentenyl diphosphate binding mode determination
-
-
?
di-trans-poly-cis-decaprenyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
di-trans-poly-cis-decaprenyl diphosphate is farnesyl diphosphate, isopentenyl diphosphate binding mode determination
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
-
consecutive condensation of 8 molecules of isopentenyl diphosphate with farnesyl diphosphate to form the lipid carrier undecaprenyl diphosphate to mediate bacterial peptidoglycan synthesis
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
consecutive condensation of 8 molecules of isopentenyl diphosphate with farnesyl diphosphate to form the lipid carrier undecaprenyl diphosphate to mediate bacterial peptidoglycan synthesis
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
-
consecutive condensation of 8 molecules of isopentenyl diphosphate with farnesyl diphosphate to form the lipid carrier undecaprenyl diphosphate to mediate bacterial peptidoglycan synthesis, the final product has C55 chain length
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
-
consecutive condensation of 8 molecules of isopentenyl diphosphate with farnesyl diphosphate to form the lipid carrier undecaprenyl diphosphate to mediate bacterial peptidoglycan synthesis, the final product has C55-C60 chain length, molecular 3D-structural modeling of the reaction product
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
stereochemistry of the reaction
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
-
the phosphate head group of farnesyl diphosphate is bound to the positively charged Arg residues and the hydrocarbon moiety interacts with hydrophobic amino acids including L85, L88, and F89, located on the alpha3-helix of the enzyme
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
-
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
sequential condensation of 8 molecules of isopentenyl diphosphate in the cis-configuration into farnesyl diphosphate to produce undecaprenyl diphosphate, indispensable for the biosynthesis of bacterial cell wall
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
sequential condensation of 8 molecules of isopentenyl diphosphate in the cis-configuration into farnesyl diphosphate to produce undecaprenyl diphosphate, indispensable for the biosynthesis of bacterial cell wall
-
-
?
isopentenyl diphosphate + (E,E)-(2-diazo-3-trifluoropropionyloxy)geranyl diphosphate
(E,E)-(2-diazo-3-trifluoropropionyloxy)polyprenyl diphosphate + diphosphate
-
-
-
-
?
isopentenyl diphosphate + (E,E)-(2-diazo-3-trifluoropropionyloxy)geranyl diphosphate
(E,E)-(2-diazo-3-trifluoropropionyloxy)polyprenyl diphosphate + diphosphate
-
47% of the activity with trans,trans-farnesyl diphosphate
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
(E,E)-farnesyl diphosphate or (Z,E)-farnesyl diphosphate
C50-polyprenyl diphosphate and C55-polyprenyl diphosphate in the ratio of 3:1 from (Z,E,E,E)-farnesylgeranyl diphosphate and in the ratio 3:2 from (Z,Z,E,E)-farnesylgeranyl diphosphate, C50-polyprenyl diphosphate and C55-polyprenyl diphosphate with Z,E mixed stereochemistry, formation of C50-polyprenyl diphosphate and C55-polyprenyl diphosphate in the ratio of 1:4 from (E,E)-farnesyl diphosphate and in the ratio of 4:1 from (Z,E)-farnesyl diphosphate
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
(Z,E,E,E)-farnesylgeranyl diphosphate or (Z,Z,E,E)-farnesylgeranyl diphosphate
C50-polyprenyl diphosphate and C55-polyprenyl diphosphate in the ratio of 3:1 from (Z,E,E,E)-farnesylgeranyl diphosphate and in the ratio 3:2 from (Z,Z,E,E)-farnesylgeranyl diphosphate, C50-polyprenyl diphosphate and C55-polyprenyl diphosphate with Z,E mixed stereochemistry, formation of C50-polyprenyl diphosphate and C55-polyprenyl diphosphate in the ratio of 1:4 from (E,E)-farnesyl diphosphate and in the ratio of 4:1 from (Z,E)-farnesyl diphosphate
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
the major product of the wild-type enzyme, and mutant enzymes H103A, V103A, V105A and I62A in presence of Triton is C55-polyprenyl diphosphate. Mutant enzyme L137A produces C55-polyprenyl diphosphate, C60-polyprenyl diphosphate and C65-polyprenyl diphosphate in the ration 55:41:4
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
product distribution under various reaction conditions. In the presence of excess farnesyl diphosphate the intermediates C25-C50 accumulate
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
with 0.02% Triton X-100 the main product is the C55-compound, C50-compound is the minor product. With 0.1% Triton X-100 the C50-polyprenyl diphosphate is the main product, the C55-polyprenyl diphosphate and the C45-polyprenyl diphosphate are minor products. With 0.5% Triton X-100 the C50-polyprenyl diphosphate compound and the C45-compound are the main products, the C55-compound is not formed
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
trans,trans-farnesyl diphosphate
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
major products are undecaprenol and probably a longer chain polyprenol
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
cis,trans-farnesyl diphosphate
C55-compound is formed as major product from trans,trans-farnesyl diphosphate, the C50-compound is formed as the major product from cis,trans-farnesyl diphosphate
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
farnesyl diphosphate with mixed stereochemistry or trans,trans stereochemistry
C55-polyprenyl diphosphate is the major product
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
trans,trans-farnesyl diphosphate and cis,trans-farnesyl diphosphate
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
trans,trans-farnesyl diphosphate
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
trans,trans-farnesyl diphosphate
C55 polyprenyl diphosphate with isoprene residues with cis stereochemistry
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
trans,trans-farnesyl diphosphate
C55-compound is formed as major product from trans,trans-farnesyl diphosphate, the C50-compound is formed as the major product from cis,trans-farnesyl diphosphate
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
cis,trans-farnesyl diphosphate
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
(E,E)-farnesyl diphosphate
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
(Z,E,E)-farnesyl diphosphate
E193Q, R197S, E201Q, R203S, D221A, and D226A show product distribution pattern similar to that of the wild-type enzyme, which produces C55 prenyl diphosphate as its major product as well as minor amounts of some intermediates having shorter prenyl chains and C60 product. The major products of the mutant enzymes S74A and E216Q contain C35 and C50 prenyl chain length. Mutant enzyme F73A produces a mixture of C30 and C35 products
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
trans,trans-farnesyl diphosphate
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
trans,trans-farnesyl diphosphate
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
trans,trans-farnesyl diphosphate
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
(E,E)-farnesyl diphosphate
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
(Z,E,E)-farnesyl diphosphate
E193Q, R197S, E201Q, R203S, D221A, and D226A show product distribution pattern similar to that of the wild-type enzyme, which produces C55 prenyl diphosphate as its major product as well as minor amounts of some intermediates having shorter prenyl chains and C60 product. The major products of the mutant enzymes S74A and E216Q contain C35 and C50 prenyl chain length. Mutant enzyme F73A produces a mixture of C30 and C35 products
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
the C55 polymer is the major product in presence of Triton X-100, without Triton C55-C75 polyprenyl diphosphates are generated
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
Salmonella newington
-
-
-
-
?
isopentenyl diphosphate + geranyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
-
?
isopentenyl diphosphate + geranyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
-
?
isopentenyl diphosphate + geranyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
the C50-compound is the major product
?
isopentenyl diphosphate + geranyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
about 20% of the activity with farnesyl diphosphate
C55-polyprenyl diphosphate is the major product
?
isopentenyl diphosphate + geranyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
-
?
isopentenyl diphosphate + geranylgeranyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
-
?
isopentenyl diphosphate + geranylgeranyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
(E,E,E)-geranylgeranyl diphosphate or (Z,E,E)-geranylgeranyl diphosphate
C50-prenyl diphosphate and C55-prenyl diphosphate in the ratio of 2:3 from (E,E,E)-geranyl diphosphate and in the ratio 1:3 from (Z,E,E)-geranylgeranyl diphosphate
?
isopentenyl diphosphate + geranylgeranyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
-
?
isopentenyl diphosphate + geranylgeranyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
-
?
isopentenyl diphosphate + geranylgeranyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
trans,trans,trans-geranylgeranyl diphosphate and cis,trans,trans-geranylgeranyl diphosphate
the C55-compound is formed as major product
?
isopentenyl diphosphate + geranylgeranyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
trans,trans,trans-geranylgeranyl diphosphate
-
-
?
isopentenyl diphosphate + geranylgeranyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
-
?
isopentenyl diphosphate + geranylgeranyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
?
isopentenyl diphosphate + geranylgeranyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
(Z,E,E)-geranylgeranyl diphosphate
-
-
?
isopentenyl diphosphate + geranylgeranyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
trans,trans,trans-geranylgeranyl diphosphate and cis,trans,trans-geranylgeranyl diphosphate
-
-
?
isopentenyl diphosphate + geranylgeranyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
(Z,E,E)-geranylgeranyl diphosphate
-
-
?
isopentenyl diphosphate + geranylgeranyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
?
isopentenyl diphosphate + geranylgeranyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
-
?
isopentenyl diphosphate + geranylgeranyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
(Z,E,E)-geranylgeranyl diphosphate
-
-
?
isopentenyl diphosphate + neryl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
-
?
isopentenyl diphosphate + neryl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
C45 prenyl diphosphate, C50 prenyl diphosphate and C55 prenyl diphosphate in the ratio of 2:10:1
?
isopentenyl diphosphate + neryl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
-
?
isopentenyl diphosphate + neryl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
the C50-compound is the major product
?
isopentenyl diphosphate + neryl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
-
?
additional information
?
-
-
involved in the biosynthesis of long-chain polyprenyl diphosphate required as a carbohydrate carrier in the biosynthesis of a variety of bacterial cell envelope components
-
-
?
additional information
?
-
-
kinetic experiments with artificial substrate homologues
-
-
?
additional information
?
-
-
Z-isomer ZHIPP, (Z)-3-methyl-3-pentenyl diphosphate, which is not accepted as substrate by the enzyme, exhibits no inhibition on the synthase reaction
-
-
?
additional information
?
-
development of assay methods for UPPS, the difference in substrate utilization between forms of UPPS from different species has major implications for UPPS inhibitor development, assay construction, and the development of polysaccharide biosynthesis probes. 2-Nitrileanilinogeranyl diphosphate (2CNA-GPP) is a general and effective continuous probe for UPPS activity
-
-
?
additional information
?
-
-
development of assay methods for UPPS, the difference in substrate utilization between forms of UPPS from different species has major implications for UPPS inhibitor development, assay construction, and the development of polysaccharide biosynthesis probes. 2-Nitrileanilinogeranyl diphosphate (2CNA-GPP) is a general and effective continuous probe for UPPS activity
-
-
?
additional information
?
-
development of assay methods for UPPS, the difference in substrate utilization between forms of UPPS from different species has major implications for UPPS inhibitor development, assay construction, and the development of polysaccharide biosynthesis probes. 2-Nitrileanilinogeranyl diphosphate (2CNA-GPP) is a general and effective continuous probe for UPPS activity
-
-
?
additional information
?
-
-
role of the hydrocarbon moiety of the allylic substrate in the reaction
-
-
?
additional information
?
-
-
catalyzes the consecutive condensation reactions of a farnesyl diphosphate (FPP) with eight isopentenyl diphosphates (IPP), in which new cis-double bonds are formed, to generate undecaprenyl diphosphate that serves as a lipid carrier for peptidoglycan synthesis of bacterial cell wall
-
-
?
additional information
?
-
catalyzes the consecutive condensation reactions of a farnesyl diphosphate (FPP) with eight isopentenyl diphosphates (IPP), in which new cis-double bonds are formed, to generate undecaprenyl diphosphate that serves as a lipid carrier for peptidoglycan synthesis of bacterial cell wall
-
-
?
additional information
?
-
development of assay methods for UPPS, the difference in substrate utilization between forms of UPPS from different species has major implications for UPPS inhibitor development, assay construction, and the development of polysaccharide biosynthesis probes. 2-Nitrileanilinogeranyl diphosphate (2CNA-GPP) is a general and effective continuous probe for UPPS activity. No activity with 2-amideanilinogeranyl diphosphate due to competition with diphosphate
-
-
?
additional information
?
-
-
development of assay methods for UPPS, the difference in substrate utilization between forms of UPPS from different species has major implications for UPPS inhibitor development, assay construction, and the development of polysaccharide biosynthesis probes. 2-Nitrileanilinogeranyl diphosphate (2CNA-GPP) is a general and effective continuous probe for UPPS activity. No activity with 2-amideanilinogeranyl diphosphate due to competition with diphosphate
-
-
?
additional information
?
-
development of assay methods for UPPS, the difference in substrate utilization between forms of UPPS from different species has major implications for UPPS inhibitor development, assay construction, and the development of polysaccharide biosynthesis probes. 2-Nitrileanilinogeranyl diphosphate (2CNA-GPP) is a general and effective continuous probe for UPPS activity. No activity with 2-amideanilinogeranyl diphosphate due to competition with diphosphate
-
-
?
additional information
?
-
-
involved in the biosynthesis of long-chain polyprenyl diphosphate required as a carbohydrate carrier in the biosynthesis of a variety of bacterial cell envelope components
-
-
?
additional information
?
-
-
reactivities of the allylic substrates increase with chain length: C10, C15, C20. Each new isoprene unit added has a cis-configuration
-
-
?
additional information
?
-
-
the product undecaprenyl diphosphate is indispensable for the biosynthesis of bacterial cell walls
-
-
?
additional information
?
-
the product undecaprenyl diphosphate is indispensable for the biosynthesis of bacterial cell walls
-
-
?
additional information
?
-
-
involved in the biosynthesis of long-chain polyprenyl diphosphate required as a carbohydrate carrier in the biosynthesis of a variety of bacterial cell envelope components
-
-
?
additional information
?
-
-
artificial substrate analogs, 3-desmethyl farnesyl diphosphate and 3-desmethyl Z-geranylgeranyl diphosphate are not used as substrates. The methyl group at the 3-position of the allylic substrate is important in the undecaprenyl diphosphate synthase reaction. The binding sites for the natural substrate farnesyl diphosphate and those for the intermediate allylic diphosphate, which contains the cis-prenyl unit, are different during the cis-prenyl chain elongation reaction
-
-
?
additional information
?
-
-
catalyzes the sequential cis-condensation of isopentenyl diphosphate onto (2E,6E)-farnesyl diphosphate
-
-
?
additional information
?
-
catalyzes the sequential cis-condensation of isopentenyl diphosphate onto (2E,6E)-farnesyl diphosphate
-
-
?
additional information
?
-
-
artificial substrate analogs, 3-desmethyl farnesyl diphosphate and 3-desmethyl (2Z,6E,10E)-geranylgeranyl diphosphate are not used as substrates. The methyl group at the 3-position of the allylic substrate is important in the undecaprenyl diphosphate synthase reaction. The binding sites for the natural substrate farnesyl diphosphate and those for the intermediate allylic diphosphate, which contains the cis-prenyl unit, are different during the cis-prenyl chain elongation reaction
-
-
?
additional information
?
-
-
artificial substrate analogs, 3-desmethyl farnesyl diphosphate and 3-desmethyl Z-geranylgeranyl diphosphate are not used as substrates. The methyl group at the 3-position of the allylic substrate is important in the undecaprenyl diphosphate synthase reaction. The binding sites for the natural substrate farnesyl diphosphate and those for the intermediate allylic diphosphate, which contains the cis-prenyl unit, are different during the cis-prenyl chain elongation reaction
-
-
?
additional information
?
-
-
artificial substrate analogs, 3-desmethyl farnesyl diphosphate and 3-desmethyl (2Z,6E,10E)-geranylgeranyl diphosphate are not used as substrates. The methyl group at the 3-position of the allylic substrate is important in the undecaprenyl diphosphate synthase reaction. The binding sites for the natural substrate farnesyl diphosphate and those for the intermediate allylic diphosphate, which contains the cis-prenyl unit, are different during the cis-prenyl chain elongation reaction
-
-
?
additional information
?
-
-
the product undecaprenyl diphosphate is indispensable for the biosynthesis of bacterial cell walls
-
-
?
additional information
?
-
the product undecaprenyl diphosphate is indispensable for the biosynthesis of bacterial cell walls
-
-
?
additional information
?
-
-
catalyzes the sequential cis-condensation of isopentenyl diphosphate onto (2E,6E)-farnesyl diphosphate
-
-
?
additional information
?
-
catalyzes the sequential cis-condensation of isopentenyl diphosphate onto (2E,6E)-farnesyl diphosphate
-
-
?
additional information
?
-
-
the synthesized long-chain dehydrodolichyl diphosphate serves as a precursor of glycosyl carrier in glycoprotein biosynthesis in eukaryotes
-
-
?
additional information
?
-
the precursor for C55-P, undecaprenyl diphosphate (UPP), is synthesized by the addition of eight C5 isopentenyl units (cis[Z]-configuration) onto C15-PP (all-trans [E])-farnesyl diphosphate (FPP) catalyzed by UPP synthase
-
-
?
additional information
?
-
-
the precursor for C55-P, undecaprenyl diphosphate (UPP), is synthesized by the addition of eight C5 isopentenyl units (cis[Z]-configuration) onto C15-PP (all-trans [E])-farnesyl diphosphate (FPP) catalyzed by UPP synthase
-
-
?
additional information
?
-
the precursor for C55-P, undecaprenyl diphosphate (UPP), is synthesized by the addition of eight C5 isopentenyl units (cis[Z]-configuration) onto C15-PP (all-trans [E])-farnesyl diphosphate (FPP) catalyzed by UPP synthase
-
-
?
additional information
?
-
development of assay methods for UPPS, the difference in substrate utilization between forms of UPPS from different species has major implications for UPPS inhibitor development, assay construction, and the development of polysaccharide biosynthesis probes. 2-Nitrileanilinogeranyl diphosphate (2CNA-GPP) is a general and effective continuous probe for UPPS activity. No activity with 2-amideanilinogeranyl diphosphate due to competition with diphosphate
-
-
?
additional information
?
-
-
development of assay methods for UPPS, the difference in substrate utilization between forms of UPPS from different species has major implications for UPPS inhibitor development, assay construction, and the development of polysaccharide biosynthesis probes. 2-Nitrileanilinogeranyl diphosphate (2CNA-GPP) is a general and effective continuous probe for UPPS activity. No activity with 2-amideanilinogeranyl diphosphate due to competition with diphosphate
-
-
?
additional information
?
-
development of assay methods for UPPS, the difference in substrate utilization between forms of UPPS from different species has major implications for UPPS inhibitor development, assay construction, and the development of polysaccharide biosynthesis probes. 2-Nitrileanilinogeranyl diphosphate (2CNA-GPP) is a general and effective continuous probe for UPPS activity. No activity with 2-amideanilinogeranyl diphosphate due to competition with diphosphate
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
catalyzes the condensation of eight molecules of isopentenyl pyrophosphate (IPP) with farnesyl diphosphate (FPP) to generate C55 undecaprenyl diphosphate. With a variety of different ratios of enzyme to substrate and FPP to IPP in the presence or absence of Triton, different product distributions are found
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
UPPS catalyzes eight consecutive condensation steps of IPP with FPP to form C55 final product
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
the enzyme is responsible for the biogenesis of undecaprenyl phosphate, an indispensable glycosyl carrier lipid in bacterial cell wall biosynthesis
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
the enzyme is responsible for the biogenesis of undecaprenyl phosphate, an indispensable glycosyl carrier lipid in bacterial cell wall biosynthesis
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
catalyzes the cis-prenyl chain elongation onto trans,trans-farnesyl diphosphate (FPP) to produce undecaprenyl diphosphate (UPP). The product undecaprenyl diphosphate is indispensable for the biosynthesis of bacterial cell walls
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
catalyzes the sequential condensation of eight molecules of isopentenyl diphosphate (IPP) in the cis-configuration into farnesyl diphosphate (FPP) to produce undecaprenyl diphosphate (UPP), which is indispensable for the biosynthesis of the bacterial cell wall
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
catalyzes the cis-prenyl chain elongation onto trans,trans-farnesyl diphosphate (FPP) to produce undecaprenyl diphosphate (UPP). The product undecaprenyl diphosphate is indispensable for the biosynthesis of bacterial cell walls
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
catalyzes the sequential condensation of eight molecules of isopentenyl diphosphate (IPP) in the cis-configuration into farnesyl diphosphate (FPP) to produce undecaprenyl diphosphate (UPP), which is indispensable for the biosynthesis of the bacterial cell wall
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
-
consecutive condensation of 8 molecules of isopentenyl diphosphate with farnesyl diphosphate to form the lipid carrier undecaprenyl diphosphate to mediate bacterial peptidoglycan synthesis
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
consecutive condensation of 8 molecules of isopentenyl diphosphate with farnesyl diphosphate to form the lipid carrier undecaprenyl diphosphate to mediate bacterial peptidoglycan synthesis
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
-
consecutive condensation of 8 molecules of isopentenyl diphosphate with farnesyl diphosphate to form the lipid carrier undecaprenyl diphosphate to mediate bacterial peptidoglycan synthesis, the final product has C55 chain length
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
-
consecutive condensation of 8 molecules of isopentenyl diphosphate with farnesyl diphosphate to form the lipid carrier undecaprenyl diphosphate to mediate bacterial peptidoglycan synthesis, the final product has C55-C60 chain length, molecular 3D-structural modeling of the reaction product
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
sequential condensation of 8 molecules of isopentenyl diphosphate in the cis-configuration into farnesyl diphosphate to produce undecaprenyl diphosphate, indispensable for the biosynthesis of bacterial cell wall
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
sequential condensation of 8 molecules of isopentenyl diphosphate in the cis-configuration into farnesyl diphosphate to produce undecaprenyl diphosphate, indispensable for the biosynthesis of bacterial cell wall
-
-
?
additional information
?
-
-
involved in the biosynthesis of long-chain polyprenyl diphosphate required as a carbohydrate carrier in the biosynthesis of a variety of bacterial cell envelope components
-
-
?
additional information
?
-
-
kinetic experiments with artificial substrate homologues
-
-
?
additional information
?
-
-
catalyzes the consecutive condensation reactions of a farnesyl diphosphate (FPP) with eight isopentenyl diphosphates (IPP), in which new cis-double bonds are formed, to generate undecaprenyl diphosphate that serves as a lipid carrier for peptidoglycan synthesis of bacterial cell wall
-
-
?
additional information
?
-
catalyzes the consecutive condensation reactions of a farnesyl diphosphate (FPP) with eight isopentenyl diphosphates (IPP), in which new cis-double bonds are formed, to generate undecaprenyl diphosphate that serves as a lipid carrier for peptidoglycan synthesis of bacterial cell wall
-
-
?
additional information
?
-
-
involved in the biosynthesis of long-chain polyprenyl diphosphate required as a carbohydrate carrier in the biosynthesis of a variety of bacterial cell envelope components
-
-
?
additional information
?
-
-
the product undecaprenyl diphosphate is indispensable for the biosynthesis of bacterial cell walls
-
-
?
additional information
?
-
the product undecaprenyl diphosphate is indispensable for the biosynthesis of bacterial cell walls
-
-
?
additional information
?
-
-
involved in the biosynthesis of long-chain polyprenyl diphosphate required as a carbohydrate carrier in the biosynthesis of a variety of bacterial cell envelope components
-
-
?
additional information
?
-
-
catalyzes the sequential cis-condensation of isopentenyl diphosphate onto (2E,6E)-farnesyl diphosphate
-
-
?
additional information
?
-
catalyzes the sequential cis-condensation of isopentenyl diphosphate onto (2E,6E)-farnesyl diphosphate
-
-
?
additional information
?
-
-
the product undecaprenyl diphosphate is indispensable for the biosynthesis of bacterial cell walls
-
-
?
additional information
?
-
the product undecaprenyl diphosphate is indispensable for the biosynthesis of bacterial cell walls
-
-
?
additional information
?
-
-
catalyzes the sequential cis-condensation of isopentenyl diphosphate onto (2E,6E)-farnesyl diphosphate
-
-
?
additional information
?
-
catalyzes the sequential cis-condensation of isopentenyl diphosphate onto (2E,6E)-farnesyl diphosphate
-
-
?
additional information
?
-
-
the synthesized long-chain dehydrodolichyl diphosphate serves as a precursor of glycosyl carrier in glycoprotein biosynthesis in eukaryotes
-
-
?
additional information
?
-
the precursor for C55-P, undecaprenyl diphosphate (UPP), is synthesized by the addition of eight C5 isopentenyl units (cis[Z]-configuration) onto C15-PP (all-trans [E])-farnesyl diphosphate (FPP) catalyzed by UPP synthase
-
-
?
additional information
?
-
-
the precursor for C55-P, undecaprenyl diphosphate (UPP), is synthesized by the addition of eight C5 isopentenyl units (cis[Z]-configuration) onto C15-PP (all-trans [E])-farnesyl diphosphate (FPP) catalyzed by UPP synthase
-
-
?
additional information
?
-
the precursor for C55-P, undecaprenyl diphosphate (UPP), is synthesized by the addition of eight C5 isopentenyl units (cis[Z]-configuration) onto C15-PP (all-trans [E])-farnesyl diphosphate (FPP) catalyzed by UPP synthase
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Co2+
K+
Mg2+
Mn2+
Na+
NH4+
sulfate
-
2 molecules bound per enzyme dimer, 1 at each active site, binding structure
Triton
-
3 Triton (T1, T2, and T3) are located in the two monomers with one on the top portion of the active site tunnel in monomer A and the other two occupying the overall tunnel of monomer B
Zn2+
Co2+
-
enzyme is equally stimulated by 0.2 mM Mg2+, 0.2 mM Co2+ or 0.1 mM Mn2+
Co2+
-
enzyme is optimally stimulated by 0.1 mM Mg2+, 0.05 mM Mn2+ or 0.2 mM Co2+
Mg2+
-
required, best at 0.5 mM MgCl2, 2 Mg2+ are bound at the subunit interface, binding structure
Mg2+
-
required, enzyme utilizes a Asp-rich motif for substrate binding via Mg2+
Mg2+
role of the metal ion in catalysis, required for binding of isopentenyl diphosphate to the enzyme, best at 1 mM, low activity at 50 mM, Asp26 is required for efficient binding, Mg2+ is bound to the diphosphate of farnesyl diphosphate in the wild-type enzyme, but to the diphosphate of isopentenyl diphosphate in the mutant D26A, Mg2+ is not required for the overall structure stability, overview
Mg2+
-
is chelated by His199 and Glu213 from different subunits and possibly plays astructural rather than catalytic role
Mg2+
-
required, structures of Mg2+ binding of wild-type and mutant UPPS, overview
Mg2+
-
enzyme is equally stimulated by 0.2 mM Mg2+, 0.2 mM Co2+ or 0.1 mM Mn2+
Mg2+
-
enzyme is optimally stimulated by 0.1 mM Mg2+, 0.05 mM Mn2+ or 0.2 mM Co2+
Mg2+
divalent metal ion required, Mg2+ is most effective, optimal concentration is 240 nM
Mg2+
-
required, structures of Mg2+ binding of wild-type and mutant UPPS, overview
Mg2+
required, structures of Mg2+ binding of wild-type and mutant UPPS, overview
Mn2+
-
enzyme is equally stimulated by 0.2 mM Mg2+, 0.2 mM Co2+ or 0.1 mM Mn2+
Mn2+
-
enzyme is optimally stimulated by 0.1 mM Mg2+, 0.05 mM Mn2+ or 0.2 mM Co2+
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(1-hydroxy-2-[3'-[(naphthalene-2-sulfonyl)amino][1,1'-biphenyl]-3-yl]ethane-1,1-diyl)bis(phosphonic acid)
-
(2E,6E,10E)-4-methylfarnesyl diphosphate
-
competitive inhibitor against (2Z,6E,10E)-geranylgeranyl diphosphate
(2S,3R,4S,5S,6R)-2-(3-((4-((3-(4,5-dihydro-1H-imidazol-2-yl)-phenyl)ethynyl)phenyl)ethynyl)phenoxy)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol
(2Z)-2-hydroxy-4-oxo-4-[[3-(3-phenoxyphenyl)propyl]amino]but-2-enoic acid
-
(2Z)-2-hydroxy-4-[3-[3-(octyloxy)phenoxy]phenyl]-4-oxobut-2-enoic acid
-
(2Z)-4-([3-[3-(hexyloxy)phenyl]propyl]amino)-2-hydroxy-4-oxobut-2-enoic acid
-
(2Z)-4-[3-[3-(decyloxy)phenoxy]phenyl]-2-hydroxy-4-oxobut-2-enoic acid
-
(2Z)-4-[[3-([1,1'-biphenyl]-3-yl)propyl]amino]-2-hydroxy-4-oxobut-2-enoic acid
-
(2Z,6E,10E)-4-methyl-geranylgeranyl diphosphate
-
allylic substrate homologue, competitive inhibitor against the allylic primer. It also acts as a strong noncompetitive inhibitor against isopentenyl diphosphate
(4aS,8aS)-4-hydroxy-2-oxo-1,2,4a,5,6,7,8,8a-octahydro[1,6]naphthyridine-3-carboxylic acid (4-piperidin-1-ylphenyl)amide
-
-
(E)-3-methyl-3-pentenyl diphosphate
-
reactive as substrate and competitive inhibition profile
1-[3-fluoro-4-(4-[[2-(thiophen-2-yl)-1,3-thiazol-4-yl]methyl]piperazin-1-yl)phenyl]ethan-1-one
-
1-[[3-(hexyloxy)phenyl]methyl]-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylic acid
-
2-(2-[[5-(1-benzofuran-2-yl)-4-phenyl-4H-1,2,4-triazol-3-yl]sulfanyl]acetamido)benzoic acid
-
2-[4-[(E)-2-chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethan-1-amine
-
2-[[(2E)-2-cyano-3-[1-[(naphthalen-1-yl)methyl]-1H-indol-3-yl]prop-2-enoyl]amino]benzoic acid
-
2-[[(2E)-2-cyano-3-[3-[(4-fluorophenyl)methoxy]phenyl]prop-2-enoyl]amino]benzoic acid
-
3-(2-chlorophenyl)-5-methyl-N-[4-(propan-2-yl)phenyl]-1,2-oxazole-4-carboxamide
-
3-(2-chlorophenyl)-N-(4-isopropylphenyl-5-methylisoxazole-4-carboxamide)
i.e. UK-106051, a drug-like UPPs inhibitor, UK-106051 binds to a site in the middle of this binding cleft. Substrates FPP and IPP cannot bind simultaneously to UPPs-inhibitor binary complexes
3-(4-chlorophenyl)-N'-[(2,4-dihydroxyphenyl)methyl]-1H-pyrazole-5-carbohydrazide
-
3-([1,1'-biphenyl]-3-yl)-1-(2-hydroxy-2,2-diphosphonoethyl)pyridin-1-ium
-
3-desmethyl (2Z,6E,10E)-geranylgeranyl diphosphate
-
mixed inhibition with farnesyl diphosphate, competitive inhibition with reaction intermediate (2Z,6E,10E)-geranylgeranyl diphosphate
3-desmethyl farnesyl diphosphate
-
competitive with farnesyl diphosphate, mixed inhibition with reaction intermediate (2Z,6E,10E)-geranylgeranyl diphosphate; competitive with farnesyl diphosphate, mixed inhibition with reaction intermediate (Z,E,E)-geranylgeranyl diphosphate
3-desmethyl Z-geranylgeranyl diphosphate
-
mixed inhibition with farnesyl diphosphate, competitive inhibition with reaction intermediate (Z,E,E)-geranylgeranyl diphosphate
3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-1-(2,2-diphosphonoethyl)pyridin-1-ium
-
3-[(5Z)-5-[[5-(2,4-dichlorophenyl)furan-2-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid
-
3-[5-(5,6-dihydrobenzimidazo[1,2-c]quinazolin-6-yl)-2,5-dihydrofuran-2-yl]benzenesulfonamide
4-(dibenzo[b,d]furan-4-yl)-1-(2-hydroxy-2,2-diphosphonoethyl)pyridin-1-ium
-
4-[3-[([1,1'-biphenyl]-4-carbonyl)amino]phenoxy]benzene-1,2-dicarboxylic acid
-
5-([5-[(1H-benzimidazol-2-yl)sulfanyl]furan-2-yl]methylidene)-1,3-diazinane-2,4,6-trione
-
5-benzyl-3-[1-(4-cyclohexylanilino)ethenyl]-4-hydroxy-5,6-dihydropyridin-2(1H)-one
-
5-benzyl-4-hydroxy-3-[1-[4-(1H-imidazol-1-yl)anilino]ethenyl]-5,6-dihydropyridin-2(1H)-one
-
5-benzyl-4-hydroxy-5-methyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid (4-cyclohexylphenyl)amide
-
-
5-benzyl-N-(4-cyclohexylphenyl)-4-hydroxy-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide
-
5-benzyl-N-[4-(hexyloxy)phenyl]-4-hydroxy-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide
-
5-bromo-2-[4-(6-chloro-2,3-dihydro-1H-indole-1-sulfonyl)benzamido]benzoic acid
-
5-methoxy-4-(2-methoxyethoxy)-2-[3-(octyloxy)benzamido]benzoic acid
-
-
6-benzyl-4-hydroxy-3-[1-[4-(1H-imidazol-1-yl)anilino]ethenyl]-5,6-dihydropyridin-2(1H)-one
-
7-(2,6-dimethyl-8-diphospho-2,6-octadienyloxy)-8-methyl-4-trifluoromethyl-chromen-2-one geranyl diphosphate
-
competitive inhibitor, substrate analogue prepared and utilized to study ligand interactions
7-(azepan-1-yl)-3-(4-fluorophenyl)-5-methylpyrazolo[1,5-a]pyrimidine
-
Mg2+
inhibitory at high concentrations of e.g. 50 mM; inhibitory at high concentrations of e.g. 50 mM
N-(3,5-dichlorophenyl)-4-hydroxy-2-oxo-5-phenyl-2,5-dihydro-1H-pyrrole-3-carboxamide
-
N-(3-amino-3-oxopropyl)-1-benzyl-5-(4-methylphenyl)-N-([4-[(propan-2-yl)oxy]phenyl]methyl)-1H-pyrazole-4-carboxamide
-
-
N-(3-amino-3-oxopropyl)-5-(1-benzothiophen-5-yl)-1-benzyl-N-([4-[(propan-2-yl)oxy]phenyl]methyl)-1H-pyrazole-4-carboxamide
-
-
N-(4-chlorophenyl)-4-hydroxy-2-oxo-5-phenyl-2,5-dihydro-1H-pyrrole-3-carboxamide
-
N-(4-cyclohexylphenyl)-4-hydroxy-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamide
-
N-(4-cyclohexylphenyl)-4-hydroxy-2-oxo-5-(2-phenylethyl)-2,5-dihydro-1H-pyrrole-3-carboxamide
-
N-(4-cyclohexylphenyl)-4-hydroxy-2-oxo-5-phenyl-2,5-dihydro-1H-pyrrole-3-carboxamide
-
N-([1,1'-biphenyl]-4-yl)-4-hydroxy-2-oxo-5-(2-phenylethyl)-2,5-dihydro-1H-pyrrole-3-carboxamide
-
N-[2-[(2-[1-[(3-amino-3-iminopropyl)amino]ethenyl]-1-methyl-1H-imidazol-4-yl)acetyl]-1-methyl-1H-imidazol-4-yl]-N2-(diaminomethylidene)glycinamide
N-[3-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N'-(3-phenoxyphenyl)biphenyl-4,4'-dicarboxamide
N-[3-[3,4-di(prop-1-en-2-yl)phenoxy]phenyl][1,1'-biphenyl]-4-carboxamide
-
N1,N4-bis[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-2-nitrobenzene-1,4-dicarboxamide
-
N4-(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-N4'- (3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-[1,1-biphenyl]-4,4-dicarboxamide
-
-
N4-(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-N4'-(3-(hexyloxy)-phenyl)-[1,1-biphenyl]-4,4-dicarboxamide
N4-(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-N4'-(3-methoxyphenyl)-[1,1-biphenyl]-4,4-dicarboxamide
N4-(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-N4'-3(-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-[1,1-biphenyl]-4,4-dicarboxamide
-
SO42-
competitive inhibitor with respect to (2E,6E)-farnesyl diphosphate; competitive inhibitor with respect to farnesyl diphosphate
viridicatumtoxin B
the inhibitor shows antimicrobial activity, particularly against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA), via inhibition of the UPP synthase activity
[(5Z)-5-[[5-(4-chloro-2-methylphenyl)furan-2-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid
-
[1-hydroxy-2-(3-[3-[3-(2-hydroxy-2,2-bis-phosphono-ethyl)-biphenyl-3-ylsulfamoyl]-benzenesulfonylamino]-biphenyl-3-yl)-1-phosphono-ethyl]-phosphonic acid
[1-hydroxy-2-([1(1),2(1):2(3),3(1)-terphenyl]-1(3)-yl)ethane-1,1-diyl]bis(phosphonic acid)
-
[1-hydroxy-2-([1(1),2(1):2(3),3(1)-terphenyl]-1(4)-yl)ethane-1,1-diyl]bis(phosphonic acid)
-
-
[1-hydroxy-2-([1(1),2(1):2(4),3(1)-terphenyl]-1(3)-yl)ethane-1,1-diyl]bis(phosphonic acid)
-
[1-hydroxy-2-[([1(1),2(1):2(3),3(1)-terphenyl]-1(3)-yl)oxy]ethane-1,1-diyl]bis(phosphonic acid)
-
[1-hydroxy-3-([1(1),2(1):2(2),3(1)-terphenyl]-1(3)-yl)propane-1,1-diyl]bis(phosphonic acid)
-
[1-hydroxy-3-([1(1),2(1):2(3),3(1)-terphenyl]-1(3)-yl)propane-1,1-diyl]bis(phosphonic acid)
-
[1-hydroxy-3-([1(1),2(1):2(4),3(1)-terphenyl]-1(3)-yl)propane-1,1-diyl]bis(phosphonic acid)
-
[2-([1,1'-biphenyl]-3-yl)-1-hydroxyethane-1,1-diyl]bis(phosphonic acid)
-
[2-[3-(dibenzo[b,d]furan-4-yl)phenyl]-1-hydroxy-1,1-ethanediyl]bis(phosphonic acid)
i.e. BPH-629. A pharmacophore model is designed on a known bisphosphonate BPH-629 and used to prepare an enriched compound library that was further docked into UppS conformational ensemble generated by molecular dynamics experiment. The docking results in three anthranilic acid derivatives with promising inhibitory activity against the enzyme
[2-[3-(dibenzo[b,d]furan-4-yl)phenyl]-1-hydroxyethane-1,1-diyl]bis(phosphonic acid)
-
[3-(3,4-dichlorophenyl)-4,5-dihydro-1,2-oxazole-5,5-diyl]bis(phosphonic acid)
-
[3-[4-(dibenzo[b,d]furan-4-yl)phenyl]-1-hydroxypropane-1,1-diyl]bis(phosphonic acid)
-
[hydroxy([1(1),2(1):2(3),3(1)-terphenyl]-1(3)-yl)methylene]bis(phosphonic acid)
-
[[(9-ethyl-9H-carbazol-3-yl)amino](hydroxy)methylene]bis(phosphonic acid)
-
(2S,3R,4S,5S,6R)-2-(3-((4-((3-(4,5-dihydro-1H-imidazol-2-yl)-phenyl)ethynyl)phenyl)ethynyl)phenoxy)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol
-
(2S,3R,4S,5S,6R)-2-(3-((4-((3-(4,5-dihydro-1H-imidazol-2-yl)-phenyl)ethynyl)phenyl)ethynyl)phenoxy)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol
-
-
1,4-bis(6-(1,4,5,6-tetrahydropyrimidin-2-yl)-1H-indol-2-yl)-benzene
-
1,4-bis(6-(1,4,5,6-tetrahydropyrimidin-2-yl)-1H-indol-2-yl)-benzene
-
-
2,2'-(5,5'-(1,3-phenylenebis(ethyne-2,1-diyl))bis(3-bromo-5,1-phenylene))diethanamine
-
2,2'-(5,5'-(1,3-phenylenebis(ethyne-2,1-diyl))bis(3-bromo-5,1-phenylene))diethanamine
-
-
2,2'-(E)-ethene-1,2-diylbis[6-(4,5-dihydro-1H-imidazol-2-yl)-1H-indole]
-
2,2'-(E)-ethene-1,2-diylbis[6-(4,5-dihydro-1H-imidazol-2-yl)-1H-indole]
-
-
3-[5-(5,6-dihydrobenzimidazo[1,2-c]quinazolin-6-yl)-2,5-dihydrofuran-2-yl]benzenesulfonamide
barely inhibits UPPS of Escherichia coli; barely inhibits UPPS of Escherichia coli; i.e. HTS04781. contrary to Helicobacter pylori, HTS04781 is almost not inhibitory in Escherichia coli
3-[5-(5,6-dihydrobenzimidazo[1,2-c]quinazolin-6-yl)-2,5-dihydrofuran-2-yl]benzenesulfonamide
i.e. HTS04781, crystallization data. The sulfonamide group forms H-bonds with Gly16 and Arg26 and the N atom in the tetracyclic ring is hydrogen bound to the main chain of Met12. Extensive hydrophobic interactions are found between the tetracyclic ring with the surrounding residues including Met12, His30, Gly33 and Val34
clomiphene
inhibits the synthesis of undecaprenyl phosphate, antagonizes the activity of targocil
clomiphene
inhibits the synthesis of undecaprenyl phosphate, antagonizes the activity of targocil
MAC-0547630
the inhibitor shows great promise as a whole cell-active probe due to its selective and potent inhibition of undecaprenyl diphosphate synthase
MAC-0547630
the inhibitor shows great promise as a whole cell-active probe due to its selective and potent inhibition of undecaprenyl diphosphate synthase
MAC-0547630
the inhibitor shows great promise as a whole cell-active probe due to its selective and potent inhibition of undecaprenyl diphosphate synthase
N,N'-bis(6-chloro-1,3-benzothiazol-2-yl)methanedisulfonamide
barely inhibits UPPS of Escherichia coli; i.e. BTB06061
N,N'-bis(6-chloro-1,3-benzothiazol-2-yl)methanedisulfonamide
i.e. BTB06061, crystallization data. The sulfur atom in the thiazole ring of BTB06061 may form H-bonds with Asn15 and His30 while the SO2 group is hydrogen bound with Met12. The aromatic rings of BTB06061 form hydrophobic interactions with the surrounding hydrophobic residues, including Val34, Leu37, Ala56 and Tyr79
N-[2-[(2-[1-[(3-amino-3-iminopropyl)amino]ethenyl]-1-methyl-1H-imidazol-4-yl)acetyl]-1-methyl-1H-imidazol-4-yl]-N2-(diaminomethylidene)glycinamide
weak inhibition
N-[2-[(2-[1-[(3-amino-3-iminopropyl)amino]ethenyl]-1-methyl-1H-imidazol-4-yl)acetyl]-1-methyl-1H-imidazol-4-yl]-N2-(diaminomethylidene)glycinamide
-
weak inhibition
N-[3-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N'-(3-phenoxyphenyl)biphenyl-4,4'-dicarboxamide
-
N-[3-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N'-(3-phenoxyphenyl)biphenyl-4,4'-dicarboxamide
-
-
N1,N4-bis(4-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-2-nitroterephthalamide
-
N1,N4-bis(4-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-2-nitroterephthalamide
-
-
N1,N4-bis(4-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-2-nitroterephthalamide dihydrochloride
-
N1,N4-bis(4-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-2-nitroterephthalamide dihydrochloride
-
-
N4,N4'-bis(3-(1,4,5,6-tetrahydropyrimidin-2-yl)phenyl)biphenyl-4,4'-dicarboxamide
-
N4,N4'-bis(3-(1,4,5,6-tetrahydropyrimidin-2-yl)phenyl)biphenyl-4,4'-dicarboxamide
-
-
N4,N4'-bis(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-[1,1'-biphenyl]-4,4'-bicarboxamide
i.e. BPH-1358
N4,N4'-bis(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-[1,1'-biphenyl]-4,4'-bicarboxamide
-
i.e. BPH-1358
N4,N4'-bis(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)biphenyl-4,4'-bis(carbothioamide)
-
N4,N4'-bis(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)biphenyl-4,4'-bis(carbothioamide)
-
-
N4-(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-N4'-(3-(hexyloxy)-phenyl)-[1,1-biphenyl]-4,4-dicarboxamide
-
N4-(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-N4'-(3-(hexyloxy)-phenyl)-[1,1-biphenyl]-4,4-dicarboxamide
-
-
N4-(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-N4'-(3-methoxyphenyl)-[1,1-biphenyl]-4,4-dicarboxamide
-
N4-(3-(4,5-dihydro-1H-imidazol-2-yl)phenyl)-N4'-(3-methoxyphenyl)-[1,1-biphenyl]-4,4-dicarboxamide
-
-
spirohexaline
the molecule shows weak inhibitory activity against catalytically related enzymes such as bacterial octaprenyl pyrophosphate synthase and yeast dehydrodolichyl pyrophosphate synthase, indicating that the compound preferentially inhibits UPP synthase. The inhibitor shows antimicrobial activity, particularly against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA), via inhibition of the UPP synthase activity. Molecular docking and homology modeling of UPP synthase-spirohexaline complex
tetramic acid
-
the crystal structure is used for modelling with bound inhibitor tetramic acid
Triton X-100
-
C55 is retained in the active site for further elongation, whereas the kcat is increased by 190fold under steady-state condition by 0.1% Triton X-100
Triton X-100
-
marked decrease of activity when a small amount of detergent is added, activity gradually increases as further detergent is added, being fully restored when the concentration reaches 2%
viridicatumtoxin
originally isolated from Penicillium viridicatum, the molecule shows weak inhibitory activity against catalytically related enzymes such as bacterial octaprenyl pyrophosphate synthase and yeast dehydrodolichyl pyrophosphate synthase, indicating that the compound preferentially inhibits UPP synthase. The inhibitor shows antimicrobial activity, particularly against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA). Molecular modeling strongly suggests that the hydrophobic spirobicyclic ring of viridicatumtoxin interacts with three hydrophobic clefts of the active site in MRSA UPP synthase
[1-hydroxy-2-(3-[3-[3-(2-hydroxy-2,2-bis-phosphono-ethyl)-biphenyl-3-ylsulfamoyl]-benzenesulfonylamino]-biphenyl-3-yl)-1-phosphono-ethyl]-phosphonic acid
-
[1-hydroxy-2-(3-[3-[3-(2-hydroxy-2,2-bis-phosphono-ethyl)-biphenyl-3-ylsulfamoyl]-benzenesulfonylamino]-biphenyl-3-yl)-1-phosphono-ethyl]-phosphonic acid
-
-
additional information
-
Z-isomer ZHIPP, (Z)-3-methyl-3-pentenyl diphosphate, which is not accepted as substrate by the enzyme, exhibited no inhibition on the synthase reaction
-
additional information
a small-molecule screening platform for the discovery of inhibitors of undecaprenyl diphosphate synthase; small-molecule screening platform for the discovery of inhibitors of undecaprenyl diphosphate synthase
-
additional information
-
farnesol (1 mM) lacking the diphosphate does not inhibit the UPPS reaction; no inhibition by farnesol
-
additional information
screening of inhibitory activities of a series of amidine and bisamidine compounds against Staphylococcus aureus and Escherichia coli, overview
-
additional information
-
screening of inhibitory activities of a series of amidine and bisamidine compounds against Staphylococcus aureus and Escherichia coli, overview
-
additional information
antagonistic interactions in high-throughput screening and in compound mode of action studies. MIC values and fractional inhibitory concentrations of combinations of clomiphene and antibiotics against strain CA-MRSA USA 300, overview
-
additional information
-
a small-molecule screening platform for the discovery of inhibitors of undecaprenyl diphosphate synthase
-
additional information
a small-molecule screening platform for the discovery of inhibitors of undecaprenyl diphosphate synthase
-
additional information
-
virtual screening of inhibitors from a library of 58635 compounds performed
-
additional information
virtual screening of inhibitors from a library of 58635 compounds performed
-
additional information
the inhibitors tested show antimicrobial, cytotoxic, and enzyme inhibitory activities, overview
-
additional information
-
the inhibitors tested show antimicrobial, cytotoxic, and enzyme inhibitory activities, overview
-
additional information
-
screening of inhibitory activities of a series of amidine and bisamidine compounds against Staphylococcus aureus and Escherichia coli, overview
-
additional information
antagonistic interactions in high-throughput screening and in compound mode of action studies. MIC values and fractional inhibitory concentrations of combinations of clomiphene and antibiotics against strain CA-MRSA USA 300, overview
-
additional information
-
antagonistic interactions in high-throughput screening and in compound mode of action studies. MIC values and fractional inhibitory concentrations of combinations of clomiphene and antibiotics against strain CA-MRSA USA 300, overview
-
additional information
-
a small-molecule screening platform for the discovery of inhibitors of undecaprenyl diphosphate synthase
-
additional information
a small-molecule screening platform for the discovery of inhibitors of undecaprenyl diphosphate synthase
-
additional information
-
tetramic acids are selective and potent inhibitors of UPPS
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
capric acid
-
enhancement factor: 0.04 in absence of Triton X-100, 1.0 in presence of 0.1% Triton X-100
dipalmitoylphosphatidic acid
-
enhancement factor: 0.2 in absence of Triton X-100, 1.2 in presence of 0.1% Triton X-100
lauric acid
-
enhancement factor: 0.1 in absence of Triton X-100, 2.3 in presence of 0.1% Triton X-100
lysophosphatidylglycerol
-
weak effect in activating lipid-depleted enzyme
palmitic acid
-
enhancement factor: 0.8 in absence of Triton X-100, 1.4 in presence of 0.1% Triton X-100
phosphatidylserine
-
enhancement factor: 0.05 in absence of Triton X-100, 0.4 in presence of 0.1% Triton X-100
stearic acid
-
enhancement factor: 0.07 in absence of Triton X-100, 0.8 in presence of 0.1% Triton X-100
trans,trans,trans-geranylgeranyl diphosphate
-
stimulates activity with farnesyl diphosphate as substrate
trans,trans-farnesyl diphosphate
-
stimulates activity with farnesyl diphosphate as substrate
additional information
-
enzyme is inactive in absence of added effectors
-
cardiolipin
-
Lactobacillus plantarum, Escherichia coli, and bovine cardiolipin. Good activator in absence of detergent
cardiolipin
-
from bovine, enhancement factor: 0.8 in absence of Triton X-100, 0.1 in presence of 0.1% Triton X-100
myristic acid
-
enhancement factor: 0.2 in absence of Triton X-100, 2.1 in presence of 0.1% Triton X-100
oleic acid
-
enhancement factor: 0.9 in absence of Triton X-100, 1.3 in presence of 0.1% Triton X-100
phosphatidic acid
-
from egg, good activator in absence of detergent
phosphatidic acid
-
enhancement factor: 0.8 in absence of Triton X-100, 1.0 in presence of 0.1% Triton X-100
Triton
-
0.01 microM of UPPs with 5 microM of (2E,6E)-farnesyl diphosphate and 50 microM of isopentenyl diphosphate, 0.5 mM MgCl2, and 50 mM KCl in Hepes buffer (pH 7.5) is 190fold less active (0.013 s-1) for the IPP consumption in the absence of Triton
Triton
-
the UPPs steady-state kcat value in the presence of 0.1% Triton is 190fold larger than in the absence of Triton
Triton X-100
-
1.5% v/v, 2 molecules are bound in the active site tunnel of the beta-subunit, binding structure
Triton X-100
-
no activity in the activation by Triton X-100 is almost saturated at a concentration of 0.02%
Triton X-100
-
marked decrease of activity when a small amount of detergent is added, activity gradually increases as further detergent is added, being fully restored when the concentration reaches 2%
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
ditrans,polycis-undecaprenyl-diphosphate synthase [(2e,6e)-farnesyl-diphosphate specific] deficiency
SRD5A3-CDG: A patient with a novel mutation.
Retinal Degeneration
Knockdown of Dehydrodolichyl Diphosphate Synthase in the Drosophila Retina Leads to a Unique Pattern of Retinal Degeneration.
Retinal Degeneration
Selective Ablation of Dehydrodolichyl Diphosphate Synthase in Murine Retinal Pigment Epithelium (RPE) Causes RPE Atrophy and Retinal Degeneration.
Retinitis Pigmentosa
A missense mutation in DHDDS, encoding dehydrodolichyl diphosphate synthase, is associated with autosomal-recessive retinitis pigmentosa in Ashkenazi Jews.
Retinitis Pigmentosa
Selective Ablation of Dehydrodolichyl Diphosphate Synthase in Murine Retinal Pigment Epithelium (RPE) Causes RPE Atrophy and Retinal Degeneration.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0011 - 0.0015
(2E,6E)-8-(N-methyl-2-aminobenzoyloxy)-3,7-dimethyl-2,6-octandien-1-diphosphate
-
pH 7.5, 25°C
0.00017
(E,E)-(2-Diazo-3-trifluoropropionyloxy)geranyl diphosphate
-
pH 7.5, 35°C
0.00069
7-(2,6-dimethyl-8-diphospho-2,6-octadienyloxy)-8-methyl-4-trifluoromethyl-chromen-2-one geranyl diphosphate
-
alternative substrate, pH 7.5, 25°C
0.00011
(2E,6E)-farnesyl diphosphate
wild type, pH 7.5, temperature not specified in the publication
0.00015
(2E,6E)-farnesyl diphosphate
mutant C234A, pH 7.5, temperature not specified in the publication
0.00037
(2E,6E)-farnesyl diphosphate
pH 7.5, 25°C, wild type with 1 mM MgCl2
0.0004
(2E,6E)-farnesyl diphosphate
-
pH 7.5, 25°C, wild type
0.0004
(2E,6E)-farnesyl diphosphate
-
mutant enzyme W91F, pH 7.5, 25°C, wild-type enzyme, pH 7.5, 25°C
0.0004
(2E,6E)-farnesyl diphosphate
-
mutant enzymes E73A, D150A and D218A, pH 7.5, 25°C; wild-type enzyme, pH 7.5, 25°C
0.00044
(2E,6E)-farnesyl diphosphate
pH 7.5, 25°C, wild type with 3 mM MgCl2
0.00046
(2E,6E)-farnesyl diphosphate
pH 7.5, 25°C, D26K mutant with 0.5 mM MgCl2
0.00055
(2E,6E)-farnesyl diphosphate
pH 7.5, 25°C, D26R mutant with 0.5 mM MgCl2
0.00067
(2E,6E)-farnesyl diphosphate
pH 7.5, 25°C, D26E mutant with 0.5 mM MgCl2
0.0015
(2E,6E)-farnesyl diphosphate
pH 7.5, 25°C, wild type with 0.05 mM MgCl2
0.00157
(2E,6E)-farnesyl diphosphate
pH 7.5, 25°C, wild type with 50 mM MgCl2
0.0092
(2E,6E)-farnesyl diphosphate
wild type, pH 7.5, temperature not specified in the publication
0.0096
(2E,6E)-farnesyl diphosphate
mutant C234A, pH 7.5, temperature not specified in the publication
0.0104
(2E,6E)-farnesyl diphosphate
mutant enzyme N77Q, pH 7.5, 37°C
0.0139
(2E,6E)-farnesyl diphosphate
mutant enzyme N77D, pH 7.5, 37°C
0.0147
(2E,6E)-farnesyl diphosphate
mutant enzyme N77A, pH 7.5, 37°C
0.0495
(2E,6E)-farnesyl diphosphate
mutant enzyme W78I, pH 7.5, 37°C
0.1207
(2E,6E)-farnesyl diphosphate
mutant enzyme W78R, pH 7.5, 37°C
0.155
(2E,6E)-farnesyl diphosphate
mutant enzyme N78D, pH 7.5, 37°C
0.0088
(2E,6E,10E)-geranylgeranyl diphosphate
wild-type, pH 7.5, 37°C
0.064
(2E,6E,10E)-geranylgeranyl diphosphate
R33A mutant, pH 7.5, 37°C
0.0043
(2Z,6E,10E)-geranylgeranyl diphosphate
G32R mutant, pH 7.5, 37°C
0.0045
(2Z,6E,10E)-geranylgeranyl diphosphate
R42G mutant, pH 7.5, 37°C
0.005
(2Z,6E,10E)-geranylgeranyl diphosphate
mutant enzyme N77Q, pH 7.5, 37°C
0.005
(2Z,6E,10E)-geranylgeranyl diphosphate
D29A mutant, pH 7.5, 37°C
0.0059
(2Z,6E,10E)-geranylgeranyl diphosphate
G32R-R42G mutant, pH 7.5, 37°C
0.006
(2Z,6E,10E)-geranylgeranyl diphosphate
E84Q mutant, pH 7.5, 37°C
0.0061
(2Z,6E,10E)-geranylgeranyl diphosphate
R80A mutant, pH 7.5, 37°C
0.008
(2Z,6E,10E)-geranylgeranyl diphosphate
mutant enzyme N77D, pH 7.5, 37°C; mutant enzyme W78D, pH 7.5, 37°C
0.0082
(2Z,6E,10E)-geranylgeranyl diphosphate
wild-type enzyme, pH 7.5, 37°C
0.0082
(2Z,6E,10E)-geranylgeranyl diphosphate
wild-type, pH 7.5, 37°C
0.0095
(2Z,6E,10E)-geranylgeranyl diphosphate
R33A mutant, pH 7.5, 37°C
0.0102
(2Z,6E,10E)-geranylgeranyl diphosphate
mutant enzyme N77A, pH 7.5, 37°C
0.015
(2Z,6E,10E)-geranylgeranyl diphosphate
mutant enzyme W78R, pH 7.5, 37°C
0.019
(2Z,6E,10E)-geranylgeranyl diphosphate
mutant enzyme W78I, pH 7.5, 37°C
0.023
(2Z,6E,10E)-geranylgeranyl diphosphate
E76Q mutant, pH 7.5, 37°C
5.3
(2Z,6E,10E)-geranylgeranyl diphosphate
S74A mutant, pH 7.3, 37°C
5.8
(2Z,6E,10E)-geranylgeranyl diphosphate
E216Q mutant, pH 7.3, 37°C
6
(2Z,6E,10E)-geranylgeranyl diphosphate
R197S mutant, pH 7.3, 37°C
7.5
(2Z,6E,10E)-geranylgeranyl diphosphate
D226A mutant, pH 7.3, 37°C
8.1
(2Z,6E,10E)-geranylgeranyl diphosphate
E193Q mutant, pH 7.3, 37°C
8.1
(2Z,6E,10E)-geranylgeranyl diphosphate
R203S mutant, pH 7.3, 37°C
8.2
(2Z,6E,10E)-geranylgeranyl diphosphate
wild type, pH 7.3, 37°C
9.4
(2Z,6E,10E)-geranylgeranyl diphosphate
F73A mutant, pH 7.3, 37°C
17.7
(2Z,6E,10E)-geranylgeranyl diphosphate
E201Q mutant, pH 7.3, 37°C
18.1
(2Z,6E,10E)-geranylgeranyl diphosphate
D221A mutant, pH 7.3, 37°C
0.0023
(Z,E,E)-Geranylgeranyl diphosphate
mutant enzyme E76Q, pH 7.5, 37°C
0.0043
(Z,E,E)-Geranylgeranyl diphosphate
mutant enzyme G32R, pH 7.5, 37°C
0.0045
(Z,E,E)-Geranylgeranyl diphosphate
mutant enzyme R42G, pH 7.5, 37°C
0.005
(Z,E,E)-Geranylgeranyl diphosphate
mutant enzyme N77Q, pH 7.5, 37°C
0.005
(Z,E,E)-Geranylgeranyl diphosphate
mutant enzyme D29A, pH 7.5, 37°C
0.0053
(Z,E,E)-Geranylgeranyl diphosphate
mutant enzyme S74A, pH 7.3, 37°C
0.0058
(Z,E,E)-Geranylgeranyl diphosphate
mutant enzyme R216Q, pH 7.3, 37°C
0.0059
(Z,E,E)-Geranylgeranyl diphosphate
mutant enzyme G32R/R42G, pH 7.5, 37°C
0.006
(Z,E,E)-Geranylgeranyl diphosphate
mutant enzyme R197S, pH 7.3, 37°C
0.006
(Z,E,E)-Geranylgeranyl diphosphate
mutant enzyme E84Q, pH 7.5, 37°C
0.0061
(Z,E,E)-Geranylgeranyl diphosphate
mutant enzyme R80A, pH 7.5, 37°C
0.008
(Z,E,E)-Geranylgeranyl diphosphate
mutant enzyme N77D, pH 7.5, 37°C
0.008
(Z,E,E)-Geranylgeranyl diphosphate
mutant enzyme W78D, pH 7.5, 37°C
0.0081
(Z,E,E)-Geranylgeranyl diphosphate
mutant enzyme E193Q, pH 7.3, 37°C
0.0081
(Z,E,E)-Geranylgeranyl diphosphate
mutant enzyme R203S, pH 7.3, 37°C
0.0082
(Z,E,E)-Geranylgeranyl diphosphate
wild-type enzyme, pH 7.5, 37°C
0.0082
(Z,E,E)-Geranylgeranyl diphosphate
wild-type enzyme, pH 7.3, 37°C
0.0094
(Z,E,E)-Geranylgeranyl diphosphate
mutant enzyme F73A, pH 7.3, 37°C
0.0095
(Z,E,E)-Geranylgeranyl diphosphate
mutant enzyme R33A, pH 7.5, 37°C
0.0102
(Z,E,E)-Geranylgeranyl diphosphate
mutant enzyme N77A, pH 7.5, 37°C
0.015
(Z,E,E)-Geranylgeranyl diphosphate
mutant enzyme W78R, pH 7.5, 37°C
0.0177
(Z,E,E)-Geranylgeranyl diphosphate
mutant enzyme E201Q, pH 7.3, 37°C
0.0181
(Z,E,E)-Geranylgeranyl diphosphate
mutant enzyme D221A, pH 7.3, 37°C
0.019
(Z,E,E)-Geranylgeranyl diphosphate
mutant enzyme W78I, pH 7.5, 37°C
0.0004
farnesyl diphosphate
-
mutant enzymes E73A, D150A and D218A, pH 7.5, 25°C
0.0004
farnesyl diphosphate
mutant enzyme E73A, N74A and E81A, pH 7.5, 25°C
0.00066
farnesyl diphosphate
-
pH 7.5, 25°C, recombinant mutant H199A/E213A
0.0015
farnesyl diphosphate
pH 7.5, 30°C, recombinant mutant W210A
0.0028
farnesyl diphosphate
pH 7.5, 30°C, recombinant mutant Y148F
0.0083
farnesyl diphosphate
pH 7.5, 30°C, recombinant wild-type enzyme
0.0075
geranylgeranyl diphosphate
mutant enzyme D226A, pH 7.3, 37°C
0.0041
isopentenyl diphosphate
-
pH 7.5, 25°C, wild type
0.0041
isopentenyl diphosphate
-
pH 7.5, 25°C, wild-type enzyme, with farnesyl diphosphate
0.0041
isopentenyl diphosphate
-
wild type, with (2E,6E)-farnesyl diphosphate, 25°C, pH 7.5
0.0059
isopentenyl diphosphate
mutant enzyme G32R/R42G, pH 7.5, 37°C
0.0078
isopentenyl diphosphate
wild-type enzyme, pH 7.5, 37°C
0.0078
isopentenyl diphosphate
pH 7.5, 30°C, recombinant wild-type enzyme
0.0092
isopentenyl diphosphate
pH 7.5, 25°C, D26K mutant with 0.5 mM MgCl2
0.0097
isopentenyl diphosphate
pH 7.5, 25°C, wild type with 1 mM MgCl2
0.0114
isopentenyl diphosphate