title: Biosynthesis of lipstatin. Incorporation of multiply deuterium-labeled (5Z,8Z)-tetradeca-5,8-dienoic acid and octanoic acid.
abstract: 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.
authors: Lehrstuhl für Organische Chemie und Biochemie, Technische Universität München, Lichtenbergstr. 4, D-85747 Garching, Federal Republic of Germany.
authors: M
authors: M
authors: Goese
authors: W
authors: W
authors: Eisenreich
authors: E
authors: E
authors: Kupfer
authors: P
authors: P
authors: Stohler
authors: W
authors: W
authors: Weber
authors: H G
authors: HG
authors: Leuenberger
authors: A
authors: A
authors: Bacher
mesh_terms: D002210:Caprylates / Q000378:metabolism*; D003903:Deuterium; D005231:Fatty Acids, Unsaturated / Q000378:metabolism*; D005285:Fermentation; D007783:Lactones / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D013302:Streptomyces / Q000378:metabolism*
chemical_list: D002210:Caprylates; D005231:Fatty Acids, Unsaturated; D007783:Lactones; C108157:5,8-tetradecadienoic acid; C054164:lipstatin; D003903:Deuterium; C031492:octanoic acid