| Abstract
| - Three putative intermediates in the biosynthesis of the lipase inhibitor lipstatin were synthesizedin 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]-(3S,5Z,8Z)-3-hydroxytetradeca-5,8-dienoic acid (9) was shown to serve as a direct biosynthetic precursor oflipstatin. [7,8-2H2]Hexylmalonate (11) was also incorporated into lipstatin, albeit at a relativelylow rate. The leucine moiety of [13C-formyl,15N]-N-formylleucine (10) was diverted to lipstatin underloss of the 13C-labeled formyl residue.
|
