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)
SALB: XNR_1579
SMA: SAVERM_3031(cyp14)
SHY: SHJG_6336
SHO: SHJGH_6097
SDV: BN159_3154
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 283:8183-9 (2008)
DOI:10.1074/jbc.M710421200
  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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