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Literature summary for 4.2.1.143 extracted from

  • Yabe, K.; Hamasaki, T.
    Stereochemistry during aflatoxin biosynthesis: Cyclase reaction in the conversion of versiconal to versicolorin B and racemization of versiconal hemiacetal acetate (1993), Appl. Environ. Microbiol., 59, 2493-2500.
    View publication on PubMedView publication on EuropePMC
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Localization

Localization Comment Organism GeneOntology No. Textmining
cytosol
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 Aspergillus parasiticus 5829
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Organism

Organism UniProt Comment Textmining
Aspergillus parasiticus
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Aspergillus parasiticus NIAH-26
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-
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information racemic versiconal hemiacetate or racemic versiconal leads exclusively to formation of (1'R,2'S)-(-)-versicolorin B. Only (1'R,2'S)-(-)-versicolorin B, and not (1'S,2'R)-(+)antipode, serves as a substrate for desaturase activity in the following reaction of the aflatoxin biosynthetic pathway. Thus the stereoconfiguration of bis-furan moiety in aflatoxin molecules is determined by the cyclase enzyme catalyzing the reaction from versiconal to versicolorinB. Nonenzymatic racemization in both the (2'R)- and (2'S)-versiconal hemiacetate enantiomers is dependent upon the temperature and alkaline conditions Aspergillus parasiticus ?
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 ?
additional information racemic versiconal hemiacetate or racemic versiconal leads exclusively to formation of (1'R,2'S)-(-)-versicolorin B. Only (1'R,2'S)-(-)-versicolorin B, and not (1'S,2'R)-(+)antipode, serves as a substrate for desaturase activity in the following reaction of the aflatoxin biosynthetic pathway. Thus the stereoconfiguration of bis-furan moiety in aflatoxin molecules is determined by the cyclase enzyme catalyzing the reaction from versiconal to versicolorinB. Nonenzymatic racemization in both the (2'R)- and (2'S)-versiconal hemiacetate enantiomers is dependent upon the temperature and alkaline conditions Aspergillus parasiticus NIAH-26 ?
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 ?
versiconal i.e. (2S,3S)-2,4,6,8-tetrahydroxy-3-(2-hydroxyethyl)anthra[2,3-b]furan-5,10-dione Aspergillus parasiticus (-)-versicolorin B + H2O (3aR,12bS)-8,10,12-trihydroxy-1,2,3a,12b-tetrahydroanthra[2,3-b]furo[3,2-d]furan-6,11-dione ?
versiconal i.e. (2S,3S)-2,4,6,8-tetrahydroxy-3-(2-hydroxyethyl)anthra[2,3-b]furan-5,10-dione Aspergillus parasiticus NIAH-26 (-)-versicolorin B + H2O (3aR,12bS)-8,10,12-trihydroxy-1,2,3a,12b-tetrahydroanthra[2,3-b]furo[3,2-d]furan-6,11-dione ?