Reaction: (1) (1'S)-averantin + [reduced NADPHhemoprotein reductase] + O2 = (1'S,5'S)-5'-hydroxyaverantin + [oxidized NADPHhemoprotein reductase] + H2O
(2) (1'S)-averantin + [reduced NADPHhemoprotein reductase] + O2 = (1'S,5'R)-5'-hydroxyaverantin + [oxidized NADPHhemoprotein reductase] + H2O
For diagram of reaction click here.
Glossary: averantin = 1,3,6,8-tetrahydroxy-2-[(1S)-1-hydroxyhexyl]anthracene-9,10-dione
Other name(s): AVN hydroxylase; avnA (gene name); CYP60A1
Systematic name: (1'S)-averantin,[reduced NADPHhemoprotein reductase]:oxygen oxidoreductase (5'-hydroxylating)
Comments: A cytochrome P-450 (heme-thiolate) protein isolated from the saprophytic mold Aspergillus parasiticus. Involved in aflatoxin biosynthesis. Does not react with (1'R)-averantin.
Links to other databases: BRENDA, EXPASY, KEGG, Metacyc, CAS registry number:
References:
1. Yabe, K., Matsuyama, Y., Ando, Y., Nakajima, H. and Hamasaki, T. Stereochemistry during aflatoxin biosynthesis: conversion of norsolorinic acid to averufin. Appl. Environ. Microbiol. 59 (1993) 2486-2492. [PMID: 8368836]
2. Yu, J., Chang, P.K., Cary, J.W., Bhatnagar, D. and Cleveland, T.E. avnA, a gene encoding a cytochrome P-450 monooxygenase, is involved in the conversion of averantin to averufin in aflatoxin biosynthesis in Aspergillus parasiticus. Appl. Environ. Microbiol. 63 (1997) 1349-1356. [PMID: 9097431]