Reaction: (+)-epi-isozizaene + 4 reduced [2Fe-2S] ferredoxin + 4 H+ + 2 O2 = albaflavenone + 4 oxidized [2Fe-2S] ferredoxin + 3 H2O (overall reaction)
(1a) (+)-epi-isozizaene + 2 reduced [2Fe-2S] ferredoxin + 2 H+ + O2 = (5S)-albaflavenol + 2 oxidized [2Fe-2S] ferredoxin + H2O
(1b) (5S)-albaflavenol + 2 reduced [2Fe-2S] ferredoxin + 2 H+ + O2 = albaflavenone + 2 oxidized [2Fe-2S] ferredoxin + 2 H2O
(2a) (+)-epi-isozizaene + 2 reduced [2Fe-2S] ferredoxin + 2 H+ + O2 = (5R)-albaflavenol + 2 oxidized [2Fe-2S] ferredoxin + H2O
(2b) (5R)-albaflavenol + 2 reduced [2Fe-2S] ferredoxin + 2 H+ + O2 = albaflavenone + 2 oxidized [2Fe-2S] ferredoxin + 2 H2O
For diagram of reaction, click here
Glossary: (+)-epi-isozizaene = (3S,3aR,6S)-3,7,7,8-tetramethyl-2,3,4,5,6,7-hexahydro-1H-3a,6-methanoazulene
Other name(s): CYP170A1
Systematic name: (+)-epi-isozizaene,reduced-ferredoxin:oxygen oxidoreductase (5-hydroxylating)
Comments: 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.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number:
References:
1. Zhao, B., Lin, X., Lei, L., Lamb, D.C., Kelly, S.L., Waterman, M.R. and Cane, D.E. Biosynthesis of the sesquiterpene antibiotic albaflavenone in Streptomyces coelicolor A3(2). J. Biol. Chem. 283 (2008) 8183-8189. [PMID: 18234666]