420838-45-5

Upstream product

• 420838-44-4 [3-2H]-(3S)-5-hydroxy-3-tert-butyldiphenylsilyloxypentanoic acid propyl ester 
• 542-05-2 acetonedicarboxylic acid 
• 53630-64-1 dipropyl 1,3-acetonedicarboxylate 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 420838-42-2 [3-2H]-(3S)-3-hydroxyglutaric acid monopropyl ester 
• 420838-41-1 [3-2H]-3-hydroxyglutaric acid dipropyl ester 
• 420838-43-3 [3-2H]-(3S)-3-tert-butyldiphenylsilyloxyglutaric acid monopropyl ester 

Downstream Products

• 421546-82-9 [3,10,11,12-2H]-(3S,5Z,8Z)-3-tert-butyldiphenylsilyloxytetradeca-5,8-dienoic acid propyl ester 

Relevant academic research and scientific papers

Biosynthetic precursors of the lipase inhibitor lipstatin

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]-(3S,5Z,8Z)-3-hydroxytetradeca-5,8-dienoic acid (9) was shown to serve as a direct biosynthetic precursor of lipstatin. [7,8-2H2]Hexylmalonate (11) was also incorporated into lipstatin, albeit at a relatively low rate. The leucine moiety of [13C-formyl,15N]-N-formylleucine (10) was diverted to lipstatin under loss of the 13C-labeled formyl residue.