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- Name help_outline (3S)-versiconol acetate Identifier CHEBI:72673 Charge -1 Formula C20H17O9 InChIKeyhelp_outline BWYUKBCRHDFWFF-SECBINFHSA-M SMILEShelp_outline CC(=O)OCC[C@H](CO)c1c([O-])cc2C(=O)c3cc(O)cc(O)c3C(=O)c2c1O 2D coordinates Mol file for the small molecule Search links Involved in 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline NADP+ Identifier CHEBI:58349 Charge -3 Formula C21H25N7O17P3 InChIKeyhelp_outline XJLXINKUBYWONI-NNYOXOHSSA-K SMILEShelp_outline NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](OP([O-])([O-])=O)[C@@H]2O)n2cnc3c(N)ncnc23)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1,253 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline (2S,3S)-versiconal hemiacetal acetate Identifier CHEBI:77975 Charge -1 Formula C20H15O9 InChIKeyhelp_outline DYJNRRXQVSJBAA-LXGOIASLSA-M SMILEShelp_outline CC(=O)OCC[C@@H]1[C@@H](O)Oc2cc3C(=O)c4cc([O-])cc(O)c4C(=O)c3c(O)c12 2D coordinates Mol file for the small molecule Search links Involved in 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,176 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline NADPH Identifier CHEBI:57783 (Beilstein: 10411862) help_outline Charge -4 Formula C21H26N7O17P3 InChIKeyhelp_outline ACFIXJIJDZMPPO-NNYOXOHSSA-J SMILEShelp_outline NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](OP([O-])([O-])=O)[C@@H]2O)n2cnc3c(N)ncnc23)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1,247 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:35695 | RHEA:35696 | RHEA:35697 | RHEA:35698 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Participation in aflatoxin biosynthesis by a reductase enzyme encoded by vrdA gene outside the aflatoxin gene cluster.
Shima Y., Shiina M., Shinozawa T., Ito Y., Nakajima H., Adachi Y., Yabe K.
Three reactions from hydroxyversicolorone to versicolorone, from versiconal hemiacetal acetate to versiconol acetate, and from versiconal to versiconol are involved in a metabolic grid in aflatoxin biosynthesis. This work demonstrated that the same reductase of Aspergillus parasiticus catalyzes th ... >> More
Three reactions from hydroxyversicolorone to versicolorone, from versiconal hemiacetal acetate to versiconol acetate, and from versiconal to versiconol are involved in a metabolic grid in aflatoxin biosynthesis. This work demonstrated that the same reductase of Aspergillus parasiticus catalyzes the three reactions. The gene (named vrdA) encoding the reductase was cloned, and its sequence did not show homology to any regions in aflatoxin gene cluster. Its cDNA encoding a 38,566Da protein was separated by three introns in the genome. Deletion of the vrdA gene in A. parasiticus caused a significant decrease in enzyme activity, but did not affect aflatoxin productivity of the fungi. Although the vrdA gene was expressed in culture conditions conducive to aflatoxin production, it was expressed even in the aflR deletion mutant. These results suggest that the vrdA is not an aflatoxin biosynthesis gene, although it actually participates in aflatoxin biosynthesis in cells. << Less
Fungal Genet. Biol. 46:221-231(2009) [PubMed] [EuropePMC]
This publication is cited by 2 other entries.
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Purification and characterization of two versiconal hemiacetal acetate reductases involved in aflatoxin biosynthesis.
Matsushima K., Ando Y., Hamasaki T., Yabe K.
Two versiconal hemiacetal acetate (VHA) reductase activities (designated I and II), which catalyzed the reaction from VHA to versiconol acetate (VOAc) during aflatoxin biosynthesis, were purified to apparent homogeneity from the cytosol fraction of the mycelia of Aspergillus parasiticus mutant NIA ... >> More
Two versiconal hemiacetal acetate (VHA) reductase activities (designated I and II), which catalyzed the reaction from VHA to versiconol acetate (VOAc) during aflatoxin biosynthesis, were purified to apparent homogeneity from the cytosol fraction of the mycelia of Aspergillus parasiticus mutant NIAH-26 through the following chromatography steps: first, fractionation with ammonium sulfate and then fractionation in succession with phenyl-Sepharose, DEAE-Sepharose, Sephacryl S-300, hydroxylapatite, and Matrex gel Green A chromatography. VHA reductase I and VHA reductase II were completely separated at the end of the DEAE-Sepharose step. The apparent molecular masses of reductase I and reductase II were estimated (by gel filtration) to be approximately 390 kDa; their denaturing molecular masses were 39- and 40-kDa, respectively (by sodium dodecyl sulfate-polyacrylamide gel electrophoresis). Their pI values were 6.6 and 6.0, respectively (as determined by isoelectric focusing), and the optimal pH values were 8.0 and 9.0, respectively, although both enzymes exhibited a broad optimal pH range of between 7.5 and 9.0. The K(m) values of reductase I and reductase II for VHA were 35.4 and 25.4 muM, respectively. On the other hand, in the cell-free experiments involving either VHA reductase fraction and high-performance liquid chromatography, both (2'S)- and (2'R)-VOAc enantiomers were formed from racemic VHA and more of the 2'R isomer than the 2'S isomer was produced, indicating that the VHA reductase fractions have very similar stereospecificities to the substrate. << Less
Appl. Environ. Microbiol. 60:2561-2567(1994) [PubMed] [EuropePMC]
This publication is cited by 2 other entries.