KEGG   ENZYME: 1.14.13.106Help
Entry
EC 1.14.13.106              Enzyme                                 

Name
epi-isozizaene 5-monooxygenase;
CYP170A1
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
BRITE hierarchy
Sysname
(+)-epi-isozizaene,NADPH:oxygen oxidoreductase (5-hydroxylating)
Reaction(IUBMB)
(+)-epi-isozizaene + 2 NADPH + 2 H+ + 2 O2 = albaflavenone + 2 NADP+ + 3 H2O (overall reaction) [RN:R10072];
(1a) (+)-epi-isozizaene + NADPH + H+ + O2 = (5S)-albaflavenol + NADP+ + H2O [RN:R08851];
(1b) (5S)-albaflavenol + NADPH + H+ + O2 = albaflavenone + NADP+ + 2 H2O [RN:R08852];
(2a) (+)-epi-isozizaene + NADPH + H+ + O2 = (5R)-albaflavenol + NADP+ + H2O [RN:R08853];
(2b) (5R)-albaflavenol + NADPH + H+ + O2 = albaflavenone + NADP+ + 2 H2O [RN:R08854]
Reaction(KEGG)
Substrate
(+)-epi-isozizaene [CPD:C16269];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007];
(5S)-albaflavenol [CPD:C17953];
(5R)-albaflavenol [CPD:C17955]
Product
albaflavenone [CPD:C17954];
NADP+ [CPD:C00006];
H2O [CPD:C00001];
(5S)-albaflavenol [CPD:C17953];
(5R)-albaflavenol [CPD:C17955]
Comment
This cytochrome-P-450 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.
History
EC 1.14.13.106 created 2008
Pathway
ec00909  Sesquiterpenoid and triterpenoid biosynthesis
ec01130  Biosynthesis of antibiotics
Orthology
K12645  epi-isozizaene 5-monooxygenase / beta-farnesene synthase
Genes
SCO: SCO5223(SC7E4.20)
SMA: SAVERM_3031(cyp14)
SHY: SHJG_6336
SHO: SHJGH_6097
SDV: BN159_3154
SALB: XNR_1579
SALS: SLNWT_2071
SCI: B446_24615
SLV: SLIV_12250
SGU: SGLAU_22465
SLE: sle_25170(sle_25170)
STRD: NI25_13050
 » show all
Taxonomy
Reference
1  [PMID:18234666]
  Authors
Zhao B, Lin X, Lei L, Lamb DC, Kelly SL, Waterman MR, Cane DE
  Title
Biosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor A3(2).
  Journal
J. Biol. Chem. 283 (2008) 8183-9.
  Sequence
[sco:SCO5223]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.13.106
IUBMB Enzyme Nomenclature: 1.14.13.106
ExPASy - ENZYME nomenclature database: 1.14.13.106
BRENDA, the Enzyme Database: 1.14.13.106
CAS: 1207718-51-1

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