The Enzyme Database

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EC 1.1.1.352     
Accepted name: 5′-hydroxyaverantin dehydrogenase
Reaction: (1) (1′S,5′S)-hydroxyaverantin + NAD+ = 5′-oxoaverantin + NADH + H+
(2) (1′S,5′R)-hydroxyaverantin + NAD+ = 5′-oxoaverantin + NADH + H+
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
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. [DOI] [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. [DOI] [PMID: 14602595]
[EC 1.1.1.352 created 2013]
 
 
EC 4.2.1.142     
Accepted name: 5′-oxoaverantin cyclase
Reaction: 5′-oxoaverantin = (1′S,5′S)-averufin + H2O
For diagram of aflatoxin biosynthesis (part 1), click here
Glossary: 5′-oxoaverantin = 1,3,6,8-tetrahydroxy-2-[(1S)-1-hydroxy-5-oxohexyl]anthracene-9,10-dione
averufin = 7,9,11-trihydroxy-2-methyl-3,4,5,6-tetrahydro-2,6-epoxy-2H-anthra[2,3-b]oxocin-8,13-dione
Other name(s): OAVN cyclase; 5′-oxoaverantin hydro-lyase [(2′S,5′S)-averufin forming]
Systematic name: 5′-oxoaverantin hydro-lyase [(1′S,5′S)-averufin-forming]
Comments: Isolated from the aflatoxin-producing mold Aspergillus parasiticus. The enzyme also catalyses the conversion of versiconal to versicolorin B (EC 4.2.1.143, versicolorin B synthase). Involved in aflatoxin biosynthesis.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  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. [DOI] [PMID: 14602595]
2.  Sakuno, E., Wen, Y., Hatabayashi, H., Arai, H., Aoki, C., Yabe, K. and Nakajima, H. Aspergillus parasiticus cyclase catalyzes two dehydration steps in aflatoxin biosynthesis. Appl. Environ. Microbiol. 71 (2005) 2999–3006. [DOI] [PMID: 15932995]
[EC 4.2.1.142 created 2013]
 
 


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