Reaction: (1) (1'S,5'S)-hydroxyaverantin + NAD+ = 5'-oxoaverantin + NADH + H+
(2) (1'S,5'R)-hydroxyaverantin + NAD+ = 5'-oxoaverantin + NADH + H+
For diagram of reaction click here.
Glossary: 5'-oxoaverantin = 1,3,6,8-tetrahydroxy-2-[(1S)-1-hydroxy-5-oxohexyl]anthracene-9,10-dione
Other name(s): HAVN dehydrogenase; adhA (gene name)
Systematic name: (1'S,5'S)-hydroxyaverantin:NAD+ oxidoreductase
Comments: Isolated from the aflatoxin-producing mold Aspergillus parasiticus [2]. Involved in aflatoxin biosynthesis. 5'-Oxoaverantin will spontaneously form averufin by intramolecular ketalisation. cf. EC 4.2.1.142, 5'-oxoaverantin cyclase.
Links to other databases: BRENDA, EXPASY, KEGG, Metacyc, CAS registry number:
References:
1. Chang, P.K., Yu, J., Ehrlich, K.C., Boue, S.M., Montalbano, B.G., Bhatnagar, D. and Cleveland, T.E. adhA in Aspergillus parasiticus is involved in conversion of 5'-hydroxyaverantin to averufin. Appl. Environ. Microbiol. 66 (2000) 4715-4719. [PMID: 11055914]
2. Sakuno, E., Yabe, K. and Nakajima, H. Involvement of two cytosolic enzymes and a novel intermediate, 5'-oxoaverantin, in the pathway from 5'-hydroxyaverantin to averufin in aflatoxin biosynthesis. Appl. Environ. Microbiol. 69 (2003) 6418-6426. [PMID: 14602595]