Information on EC 4.2.3.7 - pentalenene synthase

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The expected taxonomic range for this enzyme is: Streptomyces

EC NUMBER
COMMENTARY
4.2.3.7
-
RECOMMENDED NAME
GeneOntology No.
pentalenene synthase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate = pentalenene + diphosphate
show the reaction diagram
mechanism
-
(2E,6E)-farnesyl diphosphate = pentalenene + diphosphate
show the reaction diagram
stereochemistry
-
(2E,6E)-farnesyl diphosphate = pentalenene + diphosphate
show the reaction diagram
stereochemistry, SE reaction type
-
(2E,6E)-farnesyl diphosphate = pentalenene + diphosphate
show the reaction diagram
the initial step in the reaction is probably a cyclization of farnesyl diphosphate to form humulene. The enzyme is involved in the biosynthesis of pentalenolactone and related antibiotics
-
-
-
(2E,6E)-farnesyl diphosphate = pentalenene + diphosphate
show the reaction diagram
mechanism, stereochemistry, stereochemistry, SE reaction type
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
P-O bond cleavage
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
neopentalenoketolactone and pentalenate biosynthesis
-
-
pentalenolactone biosynthesis
-
-
Sesquiterpenoid and triterpenoid biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl diphosphate diphosphate-lyase (cyclizing, pentalenene-forming)
Isolated from Streptomyces avermitilis. The enzyme is involved in the biosynthesis of pentalenolactone and related antibiotics. The 9si hydrogen of farnesyl diphosphate undergoes a 1,2-hydride shift where it becomes the 1alpha hydrogen of pentalenene.
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pentalenene synthetase
-
-
-
-
synthetase, pentalenene
-
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
90597-46-9
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
in this theoretical study Streptomyces is given as an example for a pentalenene synthesizing organism
SwissProt
Manually annotated by BRENDA team
Streptomyces sp. UC53 19
-
SwissProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
-
expression in Xanthophyllomyces dendrorhous with concurrent knock out of the native crtE or crtYB genes. The transformations result in white colonies, showing a complete shutdown of the carotenoid production. All the mutant strains produce the sesquiterpene pentalenene and show no difference in growth when compared to the wild-type strain
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
-
-
-
-
?
(2E,6E)-farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
Streptomyces sp. UC53 19
Q55012
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
-
-
-
-
-
2-trans,6-trans-farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
Q55012
the study describes theoretical studies on the cyclization reaction
-
-
?
2-trans,6-trans-farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
-
-
-
-
-
farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
Q55012
-
-
-
-
farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
Q55012
-
mutant H309A produces 81% pentalenene and 13.4% Delta6-protoilludene, accompanied by minor quantities of germacrene A
-
?
farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
-
the initial step in the reaction is probably a cyclization of farnesyl diphosphate to form humulene
-
?
farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
-
trans,trans
-
?
farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
-
trans,trans
-
?
farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
-
trans,trans
-
?
farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
-
the initial step in the reaction is probably a cyclization of farnesyl diphosphate to form humulene
-
?
farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
-
trans,trans
-
?
farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
Q55012
-
-
-
-
additional information
?
-
Q55012
isotopically sensitive branching experiments support a mechanism for pentalenene formation involving a 7-protoilludyl cation intermediate
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
2-trans,6-trans-farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
Q55012
the study describes theoretical studies on the cyclization reaction
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
-
-
-
?
farnesyl diphosphate
pentalenene + diphosphate
show the reaction diagram
-
-
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
-
divalent metal required, Mg2+ or Mn2+
Mg2+
-
absolute requirement
Mg2+
-
required
Mn2+
-
divalent metal required, Mg2+ or Mn2+, inhibition above 2.5 mM
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
diphosphate
-
plus pentalene: no inhibition alone, both products bind cooperatively at the active site
diphosphate
-
-
Mn2+
-
divalent metal required, Mg2+ or Mn2+, inhibition above 2.5 mM
Pentalenene plus diphosphate
-
no inhibition alone, both products bind cooperatively at the active site
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00077
(E,E)-farnesyl diphosphate
-
30C, pH 8.4
0.0003
farnesyl diphosphate
-
30C, pH 8.2
0.00031
farnesyl diphosphate
-
30C, pH 8.2
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0032
diphosphate
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.287
-
30C, pH 8.4
0.324
-
30C, pH 8.2
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
8.2 - 8.4
-
-
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
from a 60 h cell culture
Manually annotated by BRENDA team
-
from a 60 h cell culture
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
57000
-
gel filtration
648596
57000
-
-
648597
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
-
x * 41000, SDS-PAGE
?
-
x * 41000, SDS-PAGE
-
monomer
-
1 * 42500
monomer
Streptomyces sp. UC53 19
-
1 * 42500
-
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
hanging drop vapor diffusion method, using 1-1.4 M sodium citrate or 1.4-1.8 M ammonium sulfate as precipitant
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4C, crude enzyme stable for up to 6 days
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
hydroxyapatite column chromatography and Sephadex 200 gel filtration
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Xanthophyllomyces dendrorhous
-
expressed in Escherichia coli
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
H309A
-
active site mutant
F77Y
-
compared to wild type, kcat/Km value is 20fold lower
H309A
-
retains enzymatic activity, minor increase in Km-value
H309C
-
retains enzymatic activity, minor increase in Km-value
H309F
-
retains enzymatic activity, minor increase in Km-value
H309F
-
reaction products are pentalene plus varying proportions of (+)-germacrene A and protoilludene
H309S
-
retains enzymatic activity, minor increase in Km-value
N219A
-
catalytically inactive
N219D
-
compared to wild type, kcat/Km value is 3300fold lower, reaction products are pentalene plus beta-caryophyllene
N219L
-
catalytically inactive
W308F
-
reaction products are pentalene plus varying proportions of (+)-germacrene A
W308F/H309F
-
reaction products are pentalene plus varying proportions of (+)-germacrene A
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
-
production of pentalenene by expression of pentalenene synthase gene in Xanthophyllomyces dendrorhous with concurrent knock out of the native crtE or crtYB genes. Culturing the yeast in presence of dodecane traps the volatile compounds produced, and no other terpenoids are found as by products