| Synthesis and properties of (R)-2-hydroxyglutaryl-1-CoA. (R)-2-hydroxyglutaryl-5-CoA, an erroneous product of glutaconate CoA-transferase. | |
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MedLine Citation:
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PMID: 1872995 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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1) (R)-2-Hydroxyglutaryl-1-CoA was synthesised starting from (R)-5-oxotetrahydrofuran-2-carboxylic acid (gamma-lactone of (R)-2-hydroxyglutarate) which was converted to the acylchloride and condensed with N-capryloylcysteamine. The lactone ring of the resulting thiolester was opened by acid hydrolysis and the CoA derivative was obtained by transesterification. 2) Pure glutaconate CoA-transferase from Acidaminococcus fermentans catalysed the formation of the 1- and the 5-isomer of (R)-2-hydroxyglutaryl-CoA from acetyl-CoA and (R)-2-hydroxyglutarate. The isomers were separated by HPLC and characterised by their reaction with acetate under the catalysis of the CoA-transferase. V/Km for the 1-isomer was 80 times higher than that for the 5-isomer. 3) Studies with cell-free extracts from A. fermentans showed that only (R)-2-hydroxyglutaryl-1-CoA but not its 5-isomer was dehydrated to glutaconyl-1-CoA. The data indicate that (R)-2-hydroxyglutaryl-5-CoA is an erroneous product of glutaconate CoA-transferase which only occurs in vitro. |
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Authors:
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A G Klees; W Buckel |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Biological chemistry Hoppe-Seyler Volume: 372 ISSN: 0177-3593 ISO Abbreviation: Biol. Chem. Hoppe-Seyler Publication Date: 1991 May |
Date Detail:
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Created Date: 1991-09-24 Completed Date: 1991-09-24 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 8503054 Medline TA: Biol Chem Hoppe Seyler Country: GERMANY |
Other Details:
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Languages: eng Pagination: 319-24 Citation Subset: IM |
Affiliation:
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Laboratorium für Mikrobiologie, Fachbereich Biologie, Phillips-Universität Marburg. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Acyl Coenzyme A
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chemical synthesis*,
chemistry Bacteria, Anaerobic / enzymology* Catalysis Chromatography, High Pressure Liquid Coenzyme A-Transferases / chemistry* Hydrogen-Ion Concentration Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/Acyl Coenzyme A; 111769-66-5/2-hydroxyglutaryl-1-coenzyme A; 137374-53-9/2-hydroxyglutaryl-5-coenzyme A; EC 2.8.3.-/Coenzyme A-Transferases |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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