J Antibiot (Tokyo). 1987 Aug;40(8):1086-91.

Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. II. Chemistry and structure elucidation.

Hochuli E, Kupfer E, Maurer R, Meister W, Mercadal Y, Schmidt K.

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Central Research Units, F. Hoffmann-La Roche & Co., Ltd., Basel, Switzerland.

Abstract

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.

PMID:: 3680019; [PubMed - indexed for MEDLINE]

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Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. I. Producing organism, fermentation, isolation and biological activity. [J Antibiot (Tokyo). 1987]
Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. I. Producing organism, fermentation, isolation and biological activity.
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Cited by 7 PubMed Central articles

The role of acyl-coenzyme A carboxylase complex in lipstatin biosynthesis of Streptomyces toxytricini. [Appl Microbiol Biotechnol. 2010]
The role of acyl-coenzyme A carboxylase complex in lipstatin biosynthesis of Streptomyces toxytricini.
Demirev AV, Khanal A, Sedai BR, Lim SK, Na MK, Nam DH. Appl Microbiol Biotechnol. 2010 Jul; 87(3):1129-39. Epub 2010 May 2.
A concise, phosphate-mediated approach to the total synthesis of (-)-tetrahydrolipstatin. [Org Lett. 2010]
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Venukadasula PK, Chegondi R, Maitra S, Hanson PR. Org Lett. 2010 Apr 2; 12(7):1556-9.
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Pancreatic lipase inhibitory activity of taraxacum officinale in vitro and in vivo.
Zhang J, Kang MJ, Kim MJ, Kim ME, Song JH, Lee YM, Kim JI. Nutr Res Pract. 2008 Winter; 2(4):200-3. Epub 2008 Dec 31.

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