Biosynthesis of Lipstatin. Incorporation of Multiply Deuterium-Labeled (5Z,8Z)-Tetradeca-5,8-dienoic Acid and Octanoic Acid
| Autor: | Hans G. Leuenberger, Markus Goese, Peter Stohler, Ernst Kupfer, Wolfgang Eisenreich, Wolfgang A. Weber, Adelbert Bacher |
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| Rok vydání: | 2001 |
| Předmět: |
chemistry.chemical_classification
Magnetic Resonance Spectroscopy biology Chemistry Stereochemistry Organic Chemistry Streptomyces toxytricini Fatty acid Nuclear magnetic resonance spectroscopy Lipstatin Deuterium biology.organism_classification Streptomyces Lactones chemistry.chemical_compound Fermentation Fatty Acids Unsaturated Side chain Proton NMR Moiety Caprylates |
| Zdroj: | The Journal of Organic Chemistry. 66:4673-4678 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo010230b |
| Popis: | Fermentation experiments with Streptomyces toxytricini were performed using (5Z,8Z)-[10,11,12,12-(2)H]tetradeca-5,8-dienoic acid or a mixture of [2,2-(2)H(2)]- and [8,8,8-(2)H(3)]octanoic acid as supplements. (2)H NMR and mass spectroscopy confirmed the incorporation of (5Z,8Z)-[10,11,12,12-(2)H]tetradeca-5,8-dienoic acid into the C(13) side chain as well as into the C(6) side chain of lipstatin. Moreover, deuterium was incorporated into the C(6) side chain of lipstatin from the 8-position but not from the 2-position of octanoate. The data establish that the beta-lactone moiety of lipstatin is formed by condensation of a C(8) and a C(14) fatty acid with a concomitant exchange of the H-2 atoms of the C(8) fatty acid. |
| Databáze: | OpenAIRE |
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