Panclicins, novel pancreatic lipase inhibitors. II. Structural elucidation.
Panclicins A-E are novel and potent pancreatic lipase inhibitors produced by Streptomyces sp. NR 0619. Their structures have been elucidated based on NMR and FAB-MS experiments. The relative configurations have also been determined by NMR experiments. The absolute stereochemistry has been determined by the chiral HPLC analysis of the hydrolysates of panclicins A and B and by modified Mosher's method on a derivative of panclicin A. They are structurally related to beta-lactone esterase inhibitors of microbial origin, lipstatin, valilactone, ebelactones and esterastin. Panclicins also contain a beta-lactone structure with two alkyl chains, one of which has an N-formylalanyloxy or N-formylglycyloxy substituent.
Yoshinari
K
K
Nippon Roche Research Center, Kamakura, Japan.
Aoki
M
M
Ohtsuka
T
T
Nakayama
N
N
Itezono
Y
Y
Mutoh
M
M
Watanabe
J
J
Yokose
K
K
D007783:Lactones / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D008049:Lipase / Q000037:antagonists & inhibitors*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010179:Pancreas / Q000201:enzymology*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism; D013302:Streptomyces / Q000378:metabolism
D007783:Lactones; D008049:Lipase