Enzymes
| UniProtKB help_outline | 1 proteins |
| Enzyme class help_outline |
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- Name help_outline 2-epi-5-epi-valiolone 7-phosphate Identifier CHEBI:84362 Charge -2 Formula C7H11O9P InChIKeyhelp_outline WBHJALJLPRKCBI-MVIOUDGNSA-L SMILEShelp_outline O[C@@H]1[C@H](O)C(=O)C[C@@](O)(COP([O-])([O-])=O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 5-epi-valiolone 7-phosphate Identifier CHEBI:87125 Charge -2 Formula C7H11O9P InChIKeyhelp_outline WBHJALJLPRKCBI-BNHYGAARSA-L SMILEShelp_outline O[C@@H]1[C@@H](O)C(=O)C[C@@](O)(COP([O-])([O-])=O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:46932 | RHEA:46933 | RHEA:46934 | RHEA:46935 | |
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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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The acarbose-biosynthetic enzyme AcbO from Actinoplanes sp. SE 50/110 is a 2-epi-5-epi-valiolone-7-phosphate 2-epimerase.
Zhang C.S., Podeschwa M., Altenbach H.J., Piepersberg W., Wehmeier U.F.
The C7-cyclitol 2-epi-5-epi-valiolone is the first precursor of the cyclitol moiety of the alpha-glucosidase inhibitor acarbose in Actinoplanes sp. SE50. The 2-epi-5-epi-valiolone becomes phosphorylated at C7 by the ATP dependent kinase AcbM prior to the next modifications. Preliminary data gave e ... >> More
The C7-cyclitol 2-epi-5-epi-valiolone is the first precursor of the cyclitol moiety of the alpha-glucosidase inhibitor acarbose in Actinoplanes sp. SE50. The 2-epi-5-epi-valiolone becomes phosphorylated at C7 by the ATP dependent kinase AcbM prior to the next modifications. Preliminary data gave evidences that the AcbO protein could catalyse the first modification step of 2-epi-5-epi-valiolone-7-phosphate. Therefore, the AcbO protein, the encoding gene of which is also part of the acbKMLNOC operon, was overproduced and purified. Indeed the purified protein catalysed the 2-epimerisation of 2-epi-5-epi-valiolone-7-phosphate. The chemical structure of the purified reaction product was proven by nuclear magnetic resonance spectroscopy to be 5-epi-valiolone-7-phosphate. << Less