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Information on EC 1.1.1.133 - dTDP-4-dehydrorhamnose reductase
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1.1.1.133 dTDP-4-dehydrorhamnose reductaseIUBMB Comments
In the reverse direction, reduction on the 4-position of the hexose moiety takes place only while the substrate is bound to another enzyme that catalyses epimerization at C-3 and C-5; the complex has been referred to as dTDP-L-rhamnose synthase.
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Word Map
- 1.1.1.133
- dtdp-l-rhamnose
-
actinobacillus
- dttp
- actinomycetemcomitans
-
3,5-epimerase
- glucose-1-phosphate
-
s-layer
- dtdp-4-keto-6-deoxy-d-glucose
-
c-specific
-
o-antigen
-
deoxysugars
- alpha-d-glucose-1-phosphate
- dtdp-glucose-4,6-dehydratase
- dtdp-d-glucose
-
thymidylyltransferase
- oleandomycin
-
4,6-dehydratase
- synthesis
The enzyme appears in viruses and cellular organisms
Synonyms
4-ketoreductase, agl14, dtdp-4-dehydrorhamnose reductase, dtdp-6-deoxy-l-lyxo-4-hexulose reductase, dtdp-4-keto-l-rhamnose reductase, dtdp-4-keto-rhamnose reductase, thymidine diphosphate-4-dehydrorhamnose reductase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
bifunctional UDP-4-keto-6-deoxy-D-glucose epimerase/reductase
E3VXL5
-
dTDP-4-dehydrorhamnose reductase
dTDP-4-keto-L-rhamnose reductase
-
-
-
-
dTDP-4-ketorhamnose reductase
-
-
-
-
dTDP-6-deoxy-L-lyxo-4-hexulose reductase
dTDP-6-deoxy-L-mannose dehydrogenase
-
-
-
-
dTDP-L-rhamnose synthetase
-
-
-
-
RmlD
TDP-4-keto-rhamnose reductase
-
-
-
-
TDP-4-ketorhamnose reductase
-
-
-
-
thymidine diphosphate-6-deoxy-L-talose
thymidine diphospho-4-ketorhamnose reductase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
dTDP-beta-L-rhamnose + NADP+ = dTDP-4-dehydro-beta-L-rhamnose + NADPH + H+
the complex has been referred to as dTDP-L-rhamnose synthase
-
-
-
dTDP-beta-L-rhamnose + NADP+ = dTDP-4-dehydro-beta-L-rhamnose + NADPH + H+
in the reverse direction, reduction on the 4-position of the hexose moiety takes place only while the substrate is bound to another enzyme which catalyzes epimerization at C-3 and C-5
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
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reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
KEGG
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SYSTEMATIC NAME
IUBMB Comments
dTDP-6-deoxy-beta-L-mannose:NADP+ 4-oxidoreductase
In the reverse direction, reduction on the 4-position of the hexose moiety takes place only while the substrate is bound to another enzyme that catalyses epimerization at C-3 and C-5; the complex has been referred to as dTDP-L-rhamnose synthase.
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CAS REGISTRY NUMBER
COMMENTARY
37250-64-9
-
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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
dTDP-4-dehydro-6-deoxy-D-glucose + NADPH
dTDP-beta-L-rhamnose + NADP+
-
-
-
?
dTDP-4-dehydro-6-deoxy-D-glucose + NADPH + H+
dTDP-L-rhamnose + NADP+
-
-
-
?
dTDP-6-deoxy-L-lyxo-4-hexulose + NAD(P)H
dTDP-L-rhamnose + NAD(P)+
-
-
-
r
UDP-4-dehydro-6-deoxy-D-glucose + NADPH
UDP-beta-L-rhamnose + NADP+
-
-
-
?
UDP-4-keto-6-deoxy-D-glucose + NADPH + H+
UDP-L-rhamnose + NADP+
E3VXL5
-
product identification by electrospray ionization-mass spectrometry and gas chromatography mass spectrometry
-
?
additional information
?
-
no substrate: GDP-4-keto-6-deoxy-mannose, UDP-glucose, dTDP-glucose, UDP-xylose, GDP-fucose
-
-
?
dTDP-4-dehydro-6-deoxy-D-glucose + NADH + H+
dTDP-beta-L-rhamnose + NAD+
40% of the rate with NADPH
-
-
?
dTDP-4-dehydro-6-deoxy-D-glucose + NADH + H+
dTDP-beta-L-rhamnose + NAD+
-
-
-
-
?
dTDP-4-dehydro-beta-L-rhamnose + NADPH + H+
dTDP-beta-L-rhamnose + NADP+
-
-
-
?
dTDP-4-dehydro-beta-L-rhamnose + NADPH + H+
dTDP-beta-L-rhamnose + NADP+
enzyme in the dTDP-beta-L-rhamnose-biosynthetic pathway
-
-
?
dTDP-6-deoxy-L-lyxo-4-hexulose + NADPH
dTDP-L-rhamnose + NADP+
-
-
-
?
dTDP-6-deoxy-L-lyxo-4-hexulose + NADPH
dTDP-L-rhamnose + NADP+
-
-
-
?
dTDP-6-deoxy-L-lyxo-4-hexulose + NADPH
dTDP-L-rhamnose + NADP+
-
synthesis of L-rhamnose precurser dTDP-L-rhamnose, essential cell wall component of pathogenic bacteria
-
?
dTDP-6-deoxy-L-lyxo-4-hexulose + NADPH
dTDP-L-rhamnose + NADP+
-
synthesis of L-rhamnose precurser dTDP-L-rhamnose, essential cell wall component of pathogenic bacteria
-
?
dTDP-6-deoxy-L-lyxo-4-hexulose + NADPH
dTDP-L-rhamnose + NADP+
-
synthesis of L-rhamnose precurser dTDP-L-rhamnose, essential cell wall component of pathogenic bacteria
-
?
dTDP-6-deoxy-L-lyxo-4-hexulose + NADPH
dTDP-L-rhamnose + NADP+
Streptomyces mutans
-
synthesis of L-rhamnose precurser dTDP-L-rhamnose, essential cell wall component of pathogenic bacteria
-
?
dTDP-6-deoxy-L-lyxo-4-hexulose + NADPH
dTDP-L-rhamnose + NADP+
-
synthesis of L-rhamnose precurser dTDP-L-rhamnose, essential cell wall component of pathogenic bacteria
-
?
dTDP-6-deoxy-L-mannose + NADP+
dTDP-4-dehydro-6-deoxy-L-mannose + NADPH
-
-
-
-
?
dTDP-6-deoxy-L-mannose + NADP+
dTDP-4-dehydro-6-deoxy-L-mannose + NADPH
-
-
-
-
?
dTDP-6-deoxy-L-mannose + NADP+
dTDP-4-dehydro-6-deoxy-L-mannose + NADPH
-
biosynthetic pathway, overview
-
-
?
dTDP-beta-L-rhamnose + NADP+
dTDP-4-dehydro-beta-L-rhamnose + NADPH + H+
-
-
-
?
dTDP-beta-L-rhamnose + NADP+
dTDP-4-dehydro-beta-L-rhamnose + NADPH + H+
-
-
-
-
?
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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
dTDP-4-dehydro-beta-L-rhamnose + NADPH + H+
dTDP-beta-L-rhamnose + NADP+
enzyme in the dTDP-beta-L-rhamnose-biosynthetic pathway
-
-
?
dTDP-6-deoxy-L-lyxo-4-hexulose + NADPH
dTDP-L-rhamnose + NADP+
-
synthesis of L-rhamnose precurser dTDP-L-rhamnose, essential cell wall component of pathogenic bacteria
-
?
dTDP-6-deoxy-L-lyxo-4-hexulose + NADPH
dTDP-L-rhamnose + NADP+
-
synthesis of L-rhamnose precurser dTDP-L-rhamnose, essential cell wall component of pathogenic bacteria
-
?
dTDP-6-deoxy-L-lyxo-4-hexulose + NADPH
dTDP-L-rhamnose + NADP+
-
synthesis of L-rhamnose precurser dTDP-L-rhamnose, essential cell wall component of pathogenic bacteria
-
?
dTDP-6-deoxy-L-lyxo-4-hexulose + NADPH
dTDP-L-rhamnose + NADP+
Streptomyces mutans
-
synthesis of L-rhamnose precurser dTDP-L-rhamnose, essential cell wall component of pathogenic bacteria
-
?
dTDP-6-deoxy-L-lyxo-4-hexulose + NADPH
dTDP-L-rhamnose + NADP+
-
synthesis of L-rhamnose precurser dTDP-L-rhamnose, essential cell wall component of pathogenic bacteria
-
?
dTDP-6-deoxy-L-mannose + NADP+
dTDP-4-dehydro-6-deoxy-L-mannose + NADPH
-
-
-
-
?
dTDP-6-deoxy-L-mannose + NADP+
dTDP-4-dehydro-6-deoxy-L-mannose + NADPH
-
biosynthetic pathway, overview
-
-
?
dTDP-beta-L-rhamnose + NADP+
dTDP-4-dehydro-beta-L-rhamnose + NADPH + H+
-
-
-
?
dTDP-beta-L-rhamnose + NADP+
dTDP-4-dehydro-beta-L-rhamnose + NADPH + H+
-
-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADPH
based on our structural comparison of the enzyme (RfbD) with its homologs, it is found that RfbD is likely to utilize either NAD(H) or NADP(H) as a coenzyme
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
E3VXL5
divalent metal ions do not alter activity
additional information
-
the enzyme does not require metal for its activity
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
not inhibitory: MgCl2, CaCl2, EDTA at 10mM
-
additional information
-
full activity restored with up to 0.3 mM MgCl2
-
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Tuberculosis
Ensemble-based high-throughput virtual screening of natural ligands using the Super Natural-II database against cell-wall protein dTDP-4-dehydrorhamnose reductase (RmlD) in Mycobacterium tuberculosis.
Tuberculosis
Novel inhibitors of Mycobacterium tuberculosis dTDP-6-deoxy-L-lyxo-4-hexulose reductase (RmlD) identified by virtual screening.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.37
dTDP-alpha-D-glucose
-
at pH 7.5, temperature not specified in the publication
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0021
2,6,7-trihydroxy-9-(2-hydroxyphenyl)-3H-xanthen-3-one
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.0015
2,6,7-trihydroxy-9-methyl-3H-xanthen-3-one
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.0009
2,6,7-trihydroxy-9-phenyl-3H-xanthen-3-one
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
0.0025
5-ethenyl-1-methyl-9,10-dihydrophenanthrene-2,7-diol
Mycobacterium tuberculosis
-
pH and temperature not specified in the publication
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
drug target
the dTDP-beta-L-rhamnose-biosynthetic pathway is absent in humans, which make them ideal targets for therapeutic development to combat pathogens (e.g. Bacillus anthracis, the causative agent of the deadly disease Anthrax)
metabolism
enzyme in the dTDP-beta-L-rhamnose-biosynthetic pathway
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
monomer
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
vapor diffusion sitting drop method, the 2.65 A resolution crystal structure of the enzyme in complex with NADP+
hanging drop vapor diffusion method, using 12.5% (w/v) PEG 1000, 12.5% (w/v) PEG 3350, 12.5% (v/v) 2-methyl-2,4-pentanediol, 0.02 M of each carboxylic acid (0.2 M sodium formate, 0.2 M ammonium acetate, 0.2 M trisodium citrate, 0.2 M sodium potassium L-tartrate, 0.2 M sodium oxamate) and 0.1 M MES/imidazole pH 6.5
-
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
50
-
NADPH more than NADP+ prevents heat denaturation during 5 and 8 min
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
NADPH and to a lesser degree NADP+ prevent denaturation at 50°C, NAD+ and NADH are less effective
-
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, repeated freezing and thawing, loss of more than 60% of activity
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
ammonium sulfate precipitation, affinity chromatography, co-purification of enzyme I and II
-
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene L780, transcription profiling of UGER, phylogenetic analysis
E3VXL5
native overexpressed in Escherichia coli BL21(DE3) and selenomethionine-enriched in B834(lambdaDE3)
-
overexpression in Escherichia coli DH5alpha, ER2566, BL21(DE3)
-
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
synthesis
-
development and evaluation of a modular system for large scale production of important dTDP-activated deoxyhexoses from dTMP and sucrose, overview
synthesis
-
six enzymes, including the dTDP-4-keto-rhamnose reductase, are involved in the pathway and are prepared by recombinant expression in Escherichia coli for large scale production of O-antigen precursor sTDP-L-rhamnose in a one-pot reaction, overview
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Melo, A.; Glaser, L.
The mechanism of 6-deoxyhexose synthesis. II. Conversion of deoxythymidine diphosphate 4-keto-6-deoxy-D-glucose to deoxythymidine diphosphate L-rhamnose
J. Biol. Chem.
243
1475-1478
1968
Pseudomonas aeruginosa
brenda
Giraud, M.F.; McMiken, H.J.; Leonard, G.A.; Messner, P.; Whitfield, C.; Naismith, J.H.
Overexpression, purification, cry