PMID: 11925237Apr 2, 2002Paper

Biosynthetic precursors of the lipase inhibitor lipstatin

The Journal of Organic Chemistry
C A SchuhrAdelbert Bacher

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-(2)H]-(3S,5Z,8Z)-3-hydroxytetradeca-5,8-dienoic acid (9) was shown to serve as a direct biosynthetic precursor of lipstatin. [7,8-(2)H(2)]Hexylmalonate (11) was also incorporated into lipstatin, albeit at a relatively low rate. The leucine moiety of [(13)C-formyl,(15)N]-N-formylleucine (10) was diverted to lipstatin under loss of the (13)C-labeled formyl residue.

Citations

May 4, 2010·Applied Microbiology and Biotechnology·Atanas V DemirevDoo Hyun Nam
Sep 19, 2009·The Journal of Microbiology·Atanas V DemirevDoo Hyun Nam
Jul 1, 2011·The Journal of Microbiology·Atanas V DemirevDoo Hyun Nam
Sep 23, 2014·Applied and Environmental Microbiology·Tingli BaiMeifeng Tao
Sep 9, 2005·Angewandte Chemie·Carmen DrahlErik J Sorensen
Jul 11, 2014·The Journal of General and Applied Microbiology·Tingheng ZhuZhifeng Cui
Aug 28, 2020·Microbial Cell Factories·Prem ChandraPankaj Kumar Arora
Sep 8, 2018·Natural Product Reports·Serina L RobinsonLawrence P Wackett
Sep 5, 2003·Journal of Medicinal Chemistry·Wolfgang EisenreichAdelbert Bacher

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