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

(+)-epi-isozizaene,NADPH:oxygen oxidoreductase (5-hydroxylating)

(+)-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]

R08851 R08852 R08853 R08854 R10072
Reaction

(+)-epi-isozizaene [CPD:C16269];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007];
(5S)-albaflavenol [CPD:C17953];
(5R)-albaflavenol [CPD:C17955]

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.

EC 1.14.13.106 created 2008

1  [PMID:18234666]

Zhao B, Lin X, Lei L, Lamb DC, Kelly SL, Waterman MR, Cane DE

Biosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor A3(2).

J Biol Chem 283:8183-9 (2008)
DOI:10.1074/jbc.M710421200

[sco:SCO5223]