Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. II. Chemistry and structure elucidation.
The structure of a new pancreatic lipase inhibitor, lipstatin, produced by Streptomyces toxytricini was determined as (2S,3S,5S,7Z,10Z)-5-[(S)-2-formamido-4-methylpentanoyloxy ]-2-hexyl-3- hydroxy-7,10-hexadecadienoic lactone by spectroscopic and chemical methods. Structurally lipstatin is closely related to the known esterase inhibitor esterastin. It contains a N-formyl-L-leucine side chain instead of the N-acetyl-L-asparagine in esterastin.
Hochuli
E
E
Central Research Units, F. Hoffmann-La Roche & Co., Ltd., Basel, Switzerland.
Kupfer
E
E
Maurer
R
R
Meister
W
W
Mercadal
Y
Y
Schmidt
K
K
D055598:Chemical Phenomena; D002621:Chemistry; D004791:Enzyme Inhibitors; D007783:Lactones; D008049:Lipase / Q000037:antagonists & inhibitors*; D009682:Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared; D013302:Streptomyces / Q000032:analysis*
D004791:Enzyme Inhibitors; D007783:Lactones; D008049:Lipase