Information on EC 1.14.13.106 - epi-isozizaene 5-monooxygenase

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The expected taxonomic range for this enzyme is: Streptomyces coelicolor

EC NUMBER
COMMENTARY
1.14.13.106
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RECOMMENDED NAME
GeneOntology No.
epi-isozizaene 5-monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(+)-epi-isozizaene + 2 NADPH + 2 H+ + 2 O2 = albaflavenone + 2 NADP+ + 3 H2O
show the reaction diagram
overall reaction
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(+)-epi-isozizaene + NADPH + H+ + O2 = (5R)-albaflavenol + NADP+ + H2O
show the reaction diagram
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(+)-epi-isozizaene + NADPH + H+ + O2 = (5S)-albaflavenol + NADP+ + H2O
show the reaction diagram
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(5R)-albaflavenol + NADPH + H+ + O2 = albaflavenone + NADP+ + 2 H2O
show the reaction diagram
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(5S)-albaflavenol + NADPH + H+ + O2 = albaflavenone + NADP+ + 2 H2O
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Sesquiterpenoid and triterpenoid biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
(+)-epi-isozizaene,NADPH:oxygen oxidoreductase (5-hydroxylating)
This cytochrome-P450 enzyme, from the soil-dwelling bacterium Streptomyces coelicolor A3(2), catalyses two sequential allylic oxidation reactions. The substrate epi-isozizaene, which is formed by the action of EC 4.2.3.37, epi-isozizaene synthase, is first oxidized to yield the epimeric intermediates (5R)-albaflavenol and (5S)-albaflavenol, which can be further oxidized to yield the sesquiterpenoid antibiotic albaflavenone.
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
albaflavenone synthase
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albaflavenone synthase
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CYP170A1
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CYP170A1
Streptomyces coelicolor A3(2) M145
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain A3(2)
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Manually annotated by BRENDA team
Streptomyces coelicolor A3(2) M145
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-epi-isozizaene + NADPH + H+ + O2
(5R,S)-albaflavenol + NADP+ + H2O
show the reaction diagram
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?
(+)-epi-isozizaene + NADPH + H+ + O2
albaflavenone + NADP+ + H2O
show the reaction diagram
Streptomyces coelicolor, Streptomyces coelicolor A3(2) M145
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?
(5R,S)-albaflavenol + NADPH + H+ + O2
albaflavenone + NADP+ + H2O
show the reaction diagram
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?
additional information
?
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enzyme catalyses two sequential allylic oxidation reactions. The substrate epi-isozizaene is first oxidized to yield the epimeric intermediates (5R)-albaflavenol and (5S)-albaflavenol, which can be further oxidized to yield the sesquiterpenoid antibiotic albaflavenone. Proposed mechanism of biosynthesis of albaflavenone catalyzed by CYP170A1
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additional information
?
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the bifunctional enzyme is able to also generate farnesene isomers from farnesyl diphosphate: (E)-beta-farnesene (61%), (3E,6E)-alpha-farnesene (26%), (3Z,6E)-alpha-farnesene (6.8%), nerolidol (4.9%), and farnesol(1.8%)
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additional information
?
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enzyme catalyses two sequential allylic oxidation reactions. The substrate epi-isozizaene is first oxidized to yield the epimeric intermediates (5R)-albaflavenol and (5S)-albaflavenol, which can be further oxidized to yield the sesquiterpenoid antibiotic albaflavenone. Proposed mechanism of biosynthesis of albaflavenone catalyzed by CYP170A1
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additional information
?
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Streptomyces coelicolor A3(2) M145
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the bifunctional enzyme is able to also generate farnesene isomers from farnesyl diphosphate: (E)-beta-farnesene (61%), (3E,6E)-alpha-farnesene (26%), (3Z,6E)-alpha-farnesene (6.8%), nerolidol (4.9%), and farnesol(1.8%)
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(+)-epi-isozizaene + NADPH + H+ + O2
albaflavenone + NADP+ + H2O
show the reaction diagram
Streptomyces coelicolor, Streptomyces coelicolor A3(2) M145
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?
additional information
?
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Streptomyces coelicolor, Streptomyces coelicolor A3(2) M145
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the bifunctional enzyme is able to also generate farnesene isomers from farnesyl diphosphate: (E)-beta-farnesene (61%), (3E,6E)-alpha-farnesene (26%), (3Z,6E)-alpha-farnesene (6.8%), nerolidol (4.9%), and farnesol(1.8%)
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
cytochrome P-450
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cytochrome-P450
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
PDB
SCOP
CATH
ORGANISM
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
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x * 55000, SDS-PAGE
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Streptomyces coelicolor A3(2) M145
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x * 55000, SDS-PAGE
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Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Ni2+-affinity column chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
coexpression with molecular chaperones GroES/GroEL
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expressed in Escherichia coli
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
D253A/D254A/D257A
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DDXX(D/E) conserved in terpene synthases
D253A/D254A/D257A
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DDXX(D/E) conserved in terpene synthases
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D254A/D257A
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DDXX(D/E) conserved in terpene synthases
additional information
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a gene disruption mutant displays no synthesis of both albaflavenone and the albaflavenols, while epi-isozizaene is still produced
D254A/D257A
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DDXX(D/E) conserved in terpene synthases
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additional information
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a gene disruption mutant displays no synthesis of both albaflavenone and the albaflavenols, while epi-isozizaene is still produced
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