Information on EC 4.2.3.37 - epi-isozizaene synthase

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The expected taxonomic range for this enzyme is: Streptomyces

EC NUMBER
COMMENTARY
4.2.3.37
-
RECOMMENDED NAME
GeneOntology No.
epi-isozizaene synthase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate = (+)-epi-isozizaene + diphosphate
show the reaction diagram
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-
-
-
(2E,6E)-farnesyl diphosphate = (+)-epi-isozizaene + diphosphate
show the reaction diagram
ionization and isomerization of farnesyl diphosphate will give (3R)-nerolidyl diphosphate. Rotation about the newly generated C-2/C-3 bond generates the corresponding cisoid nerolidyl diphosphate conformer which can undergo ionization and cyclization to form a bisabolyl cation. Following 1,2-hydride shift and spirocyclization, the resultant acorenyl cation can undergo further cyclization, ring contraction, methyl migration, and deprotonation to yield (+)-epi-isozizaene
Q9K499
(2E,6E)-farnesyl diphosphate = (+)-epi-isozizaene + diphosphate
show the reaction diagram
ionization and isomerization of farnesyl diphosphate will give (3R)-nerolidyl diphosphate. Rotation about the newly generated C-2/C-3 bond generates the corresponding cisoid nerolidyl diphosphate conformer which can undergo ionization and cyclization to form a bisabolyl cation. Following 1,2-hydride shift and spirocyclization, the resultant acorenyl cation can undergo further cyclization, ring contraction, methyl migration, and deprotonation to yield (+)-epi-isozizaene
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-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
albaflavenone biosynthesis
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-
Biosynthesis of secondary metabolites
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-
Sesquiterpenoid and triterpenoid biosynthesis
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-
SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl-diphosphate diphosphate-lyase [(+)-epi-isozizaene-forming]
Requires Mg2+ for activity. The displacement of the diphosphate group of farnesyl diphosphate occurs with retention of configuration [1]. In the soil-dwelling bacterium Streptomyces coelicolor A3(2), the product of this reaction is used by EC 1.14.13.106, epi-isozizaene 5-monooxygenase, to produce the sesquiterpene antibiotic albaflavenone [2].
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
epi-isozizaene synthase
-
-
epi-isozizaene synthase
Q9K499
-
epi-isozizaene synthase
Q9K499
-
-
SAV_3032
Q82IV1
-
SCO5222 protein
-
-
-
-
SCO5222 protein
Q9K499
-
SCO5222 protein
Q9K499
-
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain A3(2)
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
Q82IV1
Streptomyces avermitilis does not produce epi-isozizaene or any of its oxidized derivatives, albaflavenols and albaflavenone, in any culture conditions examined. Recombinant SAV_3032 protein expressed in Escherichia coli catalyses the Mg2+-dependent cyclization of farnesyl diphosphate to epi-isozizaene
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
(+)-epi-isozizaene + diphosphate
show the reaction diagram
Q9K499
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-epi-isozizaene + diphosphate
show the reaction diagram
Q82IV1
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-epi-isozizaene + diphosphate
show the reaction diagram
-
-
major product
-
?
(2E,6E)-farnesyl diphosphate
(+)-epi-isozizaene + diphosphate
show the reaction diagram
Q9K499
-
major product (79%)
-
?
(2E,6E)-farnesyl diphosphate
(+)-epi-isozizaene + diphosphate
show the reaction diagram
-
-
major product
-
?
(2E,6E)-farnesyl diphosphate
(+)-epi-isozizaene + diphosphate
show the reaction diagram
Q9K499
-
-
-
?
(3R)-(Z)-nerolidyl diphosphate
(+)-epi-isozizaene + diphosphate
show the reaction diagram
-
>93:7 preference for (3R)-nerolidyl diphosphate over (3S)-nerolidyl diphosphate
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-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
Q82IV1
required
Mn2+
Q82IV1
32% of the activity with Mg2+
Zn2+
Q82IV1
5% of the activity with Mg2+
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.000125
(2E,6E)-farnesyl diphosphate
Q82IV1
pH 7.0, 30C
0.000147
(2E,6E)-farnesyl diphosphate
Q9K499
pH 6.5, 30C
0.00071
(2E,6E)-farnesyl diphosphate
-
wild-type protein
0.00077
(2E,6E)-farnesyl diphosphate
-
F96A mutant protein
0.0012
(2E,6E)-farnesyl diphosphate
-
F198A mutant protein
0.00145
(2E,6E)-farnesyl diphosphate
-
F203F mutant protein
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00024
(2E,6E)-farnesyl diphosphate
-
F96A mutant protein
0.00026
(2E,6E)-farnesyl diphosphate
Q82IV1
pH 7.0, 30C
0.0003
(2E,6E)-farnesyl diphosphate
-
F198A mutant protein
0.00034
(2E,6E)-farnesyl diphosphate
-
F203F mutant protein
0.045
(2E,6E)-farnesyl diphosphate
-
wild-type protein
0.049
(2E,6E)-farnesyl diphosphate
Q9K499
pH 6.5, 30C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.23
(2E,6E)-farnesyl diphosphate
-
F203F mutant protein
81
0.25
(2E,6E)-farnesyl diphosphate
-
F198A mutant protein
81
0.31
(2E,6E)-farnesyl diphosphate
-
F96A mutant protein
81
63
(2E,6E)-farnesyl diphosphate
-
wild-type protein
81
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.5
Q9K499
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
Q82IV1
assay at
PDB
SCOP
CATH
ORGANISM
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
sitting drop vapor diffusion method
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
immobilized metal ion affinity chromatography (Co2+)
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
Q82IV1
His-tagged version expressed in Escherichia coli BL21(DE3)
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
D100N
-
below 5% of wild-type activity
D99E
-
below 5% of wild-type activity
D99N
-
completely inactive
D99N
-
coordinates to Mg2+
E248D
-
below 5% of wild-type activity
F198A
-
major products: Z-gamma-bisabolene (24%), sesqusabine (20%)
F96A
-
major product: beta-farnesene (70%)
N240D
-
below 5% of wild-type activity
S244A
-
below 5% of wild-type activity
W203F
-
major product: Z-gamma-bisabolene (47%)
D100N
-
below 5% of wild-type activity
-
D99E
-
below 5% of wild-type activity
-
D99N
-
completely inactive
-
N240D
-
below 5% of wild-type activity
-
S244A
-
below 5% of wild-type activity
-