The Enzyme Database

Your query returned 4 entries.    printer_iconPrintable version



EC 1.1.1.353     
Accepted name: versiconal hemiacetal acetate reductase
Reaction: (1) versicolorone + NADP+ = 1′-hydroxyversicolorone + NADPH + H+
(2) versiconol acetate + NADP+ = versiconal hemiacetal acetate + NADPH + H+
(3) versiconol + NADP+ = versiconal + NADPH + H+
Glossary: 1′-hydroxyversicolorone = (2S,3S)-2,4,6,8-tetrahydroxy-3-(3-oxobutyl)anthra[2,3-b]furan-5,10-dione
versiconal = (2S,3S)-2,4,6,8-tetrahydroxy-3-(2-hydroxyethyl)anthra[2,3-b]furan-5,10-dione
versiconal hemiacetal acetate = 2-[(2S,3S)-2,4,6,8-tetrahydroxy-5,10-dioxo-5,10-dihydroanthra[2,3-b]furan-3-yl]ethyl acetate
versiconol = 1,3,6,8-tetrahydroxy-3-[(2S)-1,4-dihydroxybutan-2-yl]anthracene-5,10-dione
versiconol acetate = (3S)-4-hydroxy-3-[1,3,6,8-tetrahydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl]butyl acetate
versicolorone = 1,3,6,8-tetrahydroxy-2-[(2S)-1-hydroxy-5-oxohexan-2-yl]anthracene-5,10-dione
Other name(s): VHA reductase; VHA reductase I; VHA reductase II; vrdA (gene name)
Systematic name: versiconol-acetate:NADP+ oxidoreductase
Comments: Isolated from the mold Aspergillus parasiticus. Involved in a metabolic grid that leads to aflatoxin biosynthesis.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Matsushima, K., Ando, Y., Hamasaki, T. and Yabe, K. Purification and characterization of two versiconal hemiacetal acetate reductases involved in aflatoxin biosynthesis. Appl. Environ. Microbiol. 60 (1994) 2561–2567. [PMID: 16349333]
2.  Shima, Y., Shiina, M., Shinozawa, T., Ito, Y., Nakajima, H., Adachi, Y. and Yabe, K. Participation in aflatoxin biosynthesis by a reductase enzyme encoded by vrdA gene outside the aflatoxin gene cluster. Fungal Genet. Biol. 46 (2009) 221–231. [DOI] [PMID: 19211038]
[EC 1.1.1.353 created 2013]
 
 
EC 3.1.1.94     
Accepted name: versiconal hemiacetal acetate esterase
Reaction: (1) versiconal hemiacetal acetate + H2O = versiconal + acetate
(2) versiconol acetate + H2O = versiconol + acetate
For diagram of aflatoxin biosynthesis (part 2), click here
Glossary: versiconal = (2S,3S)-2,4,6,8-tetrahydroxy-3-(2-hydroxyethyl)anthra[2,3-b]furan-5,10-dione
versiconal hemiacetal acetate = 2-[(2S,3S)-2,4,6,8-tetrahydroxy-5,10-dioxo-5,10-dihydroanthra[2,3-b]furan-3-yl]ethyl acetate
versiconol = 1,3,6,8-tetrahydroxy-3-[(2S)-1,4-dihydroxybutan-2-yl]anthracene-5,10-dione
versiconol acetate = (3S)-4-hydroxy-3-[1,3,6,8-tetrahydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl]butyl acetate
Other name(s): VHA esterase
Systematic name: versiconal-hemiacetal-acetate O-acetylhydrolase
Comments: Isolated from the mold Aspergillus parasiticus. Involved in a metabolic grid that leads to aflatoxin biosynthesis.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Kusumoto, K. and Hsieh, D.P. Purification and characterization of the esterases involved in aflatoxin biosynthesis in Aspergillus parasiticus. Can. J. Microbiol. 42 (1996) 804–810. [PMID: 8776851]
2.  Chang, P.K., Yabe, K. and Yu, J. The Aspergillus parasiticus estA-encoded esterase converts versiconal hemiacetal acetate to versiconal and versiconol acetate to versiconol in aflatoxin biosynthesis. Appl. Environ. Microbiol. 70 (2004) 3593–3599. [DOI] [PMID: 15184162]
[EC 3.1.1.94 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]
 
 
EC 4.2.1.143     
Accepted name: versicolorin B synthase
Reaction: versiconal = versicolorin B + H2O
For diagram of aflatoxin biosynthesis (part 2), click here
Glossary: versiconal = (2S,3S)-2,4,6,8-tetrahydroxy-3-(2-hydroxyethyl)anthra[2,3-b]furan-5,10-dione
versicolorin B = (3aR,12bS)-8,10,12-trihydroxy-1,2,3a,12b-tetrahydroanthra[2,3-b]furo[3,2-d]furan-6,11-dione
Other name(s): versiconal cyclase; VBS
Systematic name: versiconal hydro-lyase (versicolorin-B forming)
Comments: Isolated from the aflatoxin-producing mold Aspergillus parasiticus. Involved in aflatoxin biosynthesis.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Lin, B.K. and Anderson, J.A. Purification and properties of versiconal cyclase from Aspergillus parasiticus. Arch. Biochem. Biophys. 293 (1992) 67–70. [DOI] [PMID: 1731640]
2.  McGuire, S.M., Silva, J.C., Casillas, E.G. and Townsend, C.A. Purification and characterization of versicolorin B synthase from Aspergillus parasiticus. Catalysis of the stereodifferentiating cyclization in aflatoxin biosynthesis essential to DNA interaction. Biochemistry 35 (1996) 11470–11486. [DOI] [PMID: 8784203]
3.  Silva, J.C., Minto, R.E., Barry, C.E., 3rd, Holland, K.A. and Townsend, C.A. Isolation and characterization of the versicolorin B synthase gene from Aspergillus parasiticus. Expansion of the aflatoxin b1 biosynthetic gene cluster. J. Biol. Chem. 271 (1996) 13600–13608. [DOI] [PMID: 8662689]
4.  Silva, J.C. and Townsend, C.A. Heterologous expression, isolation, and characterization of versicolorin B synthase from Aspergillus parasiticus. A key enzyme in the aflatoxin B1 biosynthetic pathway. J. Biol. Chem. 272 (1997) 804–813. [DOI] [PMID: 8995367]
[EC 4.2.1.143 created 2013]
 
 


Data © 2001–2020 IUBMB
Web site © 2005–2020 Andrew McDonald