Biosynthetic precursors of the lipase inhibitor lipstatin

…, M Goese, P Stohler, W Weber, E Kupfer…

Index: Schuhr, Christoph A.; Eisenreich, Wolfgang; Goese, Markus; Stohler, Peter; Weber, Wolfgang; Kupfer, Ernst; Bacher, Adelbert Journal of Organic Chemistry, 2002 , vol. 67, # 7 p. 2257 - 2262

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Citation Number: 20

Abstract

Three putative intermediates in the biosynthesis of the lipase inhibitor lipstatin were synthesized in stable isotope-labeled form and were added to fermentation cultures of Streptomyces toxytricini. Biosynthetic lipstatin was isolated and analyzed by NMR spectroscopy.[3, 10, 11, 12-2H]-(3 S, 5 Z, 8 Z)-3-hydroxytetradeca-5, 8-dienoic acid (9) was shown to serve as a direct biosynthetic precursor of lipstatin.[7, 8-2H2] Hexylmalonate (11) ...