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Information on EC 1.1.1.353 - versiconal hemiacetal acetate reductase for references in articles please use BRENDA:EC1.1.1.353
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EC Tree
IUBMB Comments Isolated from the mold Aspergillus parasiticus. Involved in a metabolic grid that leads to aflatoxin biosynthesis.
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
VHA reductase, VHA reductase I, VHA reductase II,
vrdA ,
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VHA reductase I
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VHA reductase II
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vrdA
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versicolorone + NADP+ = 1'-hydroxyversicolorone + NADPH + H+
(1)
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versiconol + NADP+ = versiconal + NADPH + H+
(3)
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versiconol acetate + NADP+ = versiconal hemiacetal acetate + NADPH + H+
(2)
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-
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versiconol-acetate:NADP+ oxidoreductase
Isolated from the mold Aspergillus parasiticus. Involved in a metabolic grid that leads to aflatoxin biosynthesis.
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1'-hydroxyversicolorone + NADPH + H+
versicolorone + NADP+
versiconal + NADPH + H+
versiconol + NADP+
versiconal hemiacetal acetate + NADPH + H+
versiconol acetate + NADP+
1'-hydroxyversicolorone + NADPH + H+
versicolorone + NADP+
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r
1'-hydroxyversicolorone + NADPH + H+
versicolorone + NADP+
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r
1'-hydroxyversicolorone + NADPH + H+
versicolorone + NADP+
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r
versiconal + NADPH + H+
versiconol + NADP+
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r
versiconal + NADPH + H+
versiconol + NADP+
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r
versiconal + NADPH + H+
versiconol + NADP+
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r
versiconal hemiacetal acetate + NADPH + H+
versiconol acetate + NADP+
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r
versiconal hemiacetal acetate + NADPH + H+
versiconol acetate + NADP+
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r
versiconal hemiacetal acetate + NADPH + H+
versiconol acetate + NADP+
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both (2'S)- and (2'R)-versiconol acetate enantiomers are formed from racemic versiconal hemiacetal acetate and more of the (2'R)- isomer (72-88%) than the (2'S)-isomer (12-28%) is produced
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r
versiconal hemiacetal acetate + NADPH + H+
versiconol acetate + NADP+
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r
versiconal hemiacetal acetate + NADPH + H+
versiconol acetate + NADP+
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both (2'S)- and (2'R)-versiconol acetate enantiomers are formed from racemic versiconal hemiacetal acetate and more of the (2'R)- isomer (72-88%) than the (2'S)-isomer (12-28%) is produced
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r
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versiconal + NADPH + H+
versiconol + NADP+
versiconal hemiacetal acetate + NADPH + H+
versiconol acetate + NADP+
versiconal + NADPH + H+
versiconol + NADP+
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r
versiconal + NADPH + H+
versiconol + NADP+
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r
versiconal hemiacetal acetate + NADPH + H+
versiconol acetate + NADP+
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r
versiconal hemiacetal acetate + NADPH + H+
versiconol acetate + NADP+
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both (2'S)- and (2'R)-versiconol acetate enantiomers are formed from racemic versiconal hemiacetal acetate and more of the (2'R)- isomer (72-88%) than the (2'S)-isomer (12-28%) is produced
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r
versiconal hemiacetal acetate + NADPH + H+
versiconol acetate + NADP+
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r
versiconal hemiacetal acetate + NADPH + H+
versiconol acetate + NADP+
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both (2'S)- and (2'R)-versiconol acetate enantiomers are formed from racemic versiconal hemiacetal acetate and more of the (2'R)- isomer (72-88%) than the (2'S)-isomer (12-28%) is produced
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r
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0.0254 - 0.0354
versiconal hemiacetal acetate
0.0254
versiconal hemiacetal acetate
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isoform VHA reductase II, in 60 mM potassium phosphate buffer (pH 7.5), at 37°C
0.0354
versiconal hemiacetal acetate
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isoform VHA reductase I, in 60 mM potassium phosphate buffer (pH 7.5), at 37°C
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0.00362
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crude extract, in 60 mM potassium phosphate buffer (pH 7.5), at 37°C
0.027
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isoform VHA reductase II, after 7.5fold purification, in 60 mM potassium phosphate buffer (pH 7.5), at 37°C
0.052
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isoform VHA reductase I, after 14.4fold purification, in 60 mM potassium phosphate buffer (pH 7.5), at 37°C
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8
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isoform VHA reductase I
9
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isoform VHA reductase II
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7.5 - 9
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no activity is detected below pH 4.0
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6
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isoform VHA reductase II, isoelectric focusing
6.6
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isoform VHA reductase I, isoelectric focusing
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UniProt
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metabolism
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the enzyme is specifically involved in aflatoxin biosynthesis
metabolism
the vrdA is not an aflatoxin biosynthesis gene, although it actually participates in aflatoxin biosynthesis in cells because of its group substrate specificity to intermediates in aflatoxin biosynthesis
metabolism
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the enzyme is specifically involved in aflatoxin biosynthesis
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VRDA_ASPPA
343
0
38698
Swiss-Prot
A0A0C7NTE3_DEFTU
301
0
34641
TrEMBL
A0A0H4NVF3_9BACI
300
0
34516
TrEMBL
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38566
x * 38566, calculated from amino acid sequence
39000
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10 * 39000, isoform VHA reductase I, SDS-PAGE
40000
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10 * 40000, isoform VHA reductase II, SDS-PAGE
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?
x * 38566, calculated from amino acid sequence
homodecamer
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10 * 39000, isoform VHA reductase I, SDS-PAGE; 10 * 40000, isoform VHA reductase II, SDS-PAGE
homodecamer
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10 * 39000, isoform VHA reductase I, SDS-PAGE; 10 * 40000, isoform VHA reductase II, SDS-PAGE
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ammonium sulfate fractionation, phenyl Sepharose column chromatography, DEAE-Sepharose column chromatography, Sephacryl S-300 gel filtration, hydroxylapatite column chromatography, and Matrex gel Green A chromatography
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Matsushima, K.; Ando, Y.; Hamasaki, T.; Yabe, K.
Purification and characterization of two versiconal hemiacetal acetate reductases involved in aflatoxin biosynthesis
Appl. Environ. Microbiol.
60
2561-2567
1994
Aspergillus parasiticus, Aspergillus parasiticus NUIH-26
brenda
Yabe, K.; Chihaya, N.; Hamamatsu, S.; Sakuno, E.; Hamasaki, T.; Nakajima, H.; Bennett, J.W.
Enzymatic conversion of averufin to hydroxyversicolorone and elucidation of a novel metabolic grid involved in aflatoxin biosynthesis
Appl. Environ. Microbiol.
69
66-73
2003
Aspergillus parasiticus, Aspergillus parasiticus NIAH-26
brenda
Shima, Y.; Shiina, M.; Shinozawa, T.; Ito, Y.; Nakajima, H.; Adachi, Y.; Yabe, K.
Participation in aflatoxin biosynthesis by a reductase enzyme encoded by vrdA gene outside the aflatoxin gene cluster
Fungal Genet. Biol.
46
221-231
2009
Aspergillus parasiticus (B9WYE6)
brenda
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Enzyme Nomenclature
1.1.1.353 versiconal hemiacetal acetate reductase
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