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 ACCESSION NO.
LITERATURE
(2E,6E)-farnesyl diphosphate = (+)-epi-isozizaene + diphosphate
show the reaction diagram
-
-
-
-
(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
PATHWAY
KEGG Link
MetaCyc Link
albaflavenone biosynthesis
-
Biosynthesis of secondary metabolites
-
Sesquiterpenoid and triterpenoid biosynthesis
-
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 ACCESSION NO.
COMMENTARY
LITERATURE
epi-isozizaene synthase
-
-
epi-isozizaene synthase
Q9K499
-
SAV_3032
Q82IV1
-
SCO5222 protein
-
-
-
-
SCO5222 protein
Q9K499
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
strain A3(2)
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT ACCESSION NO.
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 ACCESSION NO.
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%)
-
?
(3R)-(Z)-nerolidyl diphosphate
(+)-epi-isozizaene + diphosphate
show the reaction diagram
-
>93:7 preference for (3R)-nerolidyl diphosphate over (3S)-nerolidyl diphosphate
-
-
?
METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Mg2+
Q82IV1, -
required
Mn2+
Q82IV1, -
32% of the activity with Mg2+
Zn2+
Q82IV1, -
5% of the activity with Mg2+
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
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]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
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]
kcat/KM VALUE [1/mMs-1] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.23
-
(2E,6E)-farnesyl diphosphate
-
F203F mutant protein
263972
0.25
-
(2E,6E)-farnesyl diphosphate
-
F198A mutant protein
263972
0.31
-
(2E,6E)-farnesyl diphosphate
-
F96A mutant protein
263972
63
-
(2E,6E)-farnesyl diphosphate
-
wild-type protein
263972
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
6.5
-
Q9K499
assay at
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
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 ACCESSION NO.
LITERATURE
sitting drop vapor diffusion method
-
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
immobilized metal ion affinity chromatography (Co2+)
-
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expression in Escherichia coli
Q82IV1, -
His-tagged version expressed in Escherichia coli BL21(DE3)
-
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
D100N
-
below 5% of wild-type activity
D99E
-
below 5% of wild-type activity
D99N
-
coordinates to Mg2+
D99N
-
completely inactive
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%)