Lipstatin
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IUPAC name
[(2S,4Z,7Z)-1-[(2S,3S)-3-Hexyl-4-oxooxetan-2-yl]trideca-4,7-dien-2-yl] (2S)-2-formamido-4-methylpentanoate
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| Other names
(2S,4Z,7Z)-1-[(2S,3S)-3-Hexyl-4-oxo-2-oxetanyl]-4,7-tridecadien-2-yl N-formyl-L-leucinate
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3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.126.007 |
| MeSH | Lipstatin |
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PubChem CID
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| Properties | |
| C29H49NO5 | |
| Molar mass | 491.71 g·mol−1 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |
Lipstatin is a potent, irreversible inhibitor of pancreatic lipase. It is a natural product that was first isolated from the Actinobacterium Streptomyces toxytricini.
The popular antiobesity drug orlistat (trade names Xenical and alli) is a saturated derivative of lipstatin.
Lipstatin is composed of a 2-hexyl-3,5-dihydroxy-7,10-hexadecadienoic-β-lactone 22 carbon backbone from fatty acid synthesis pathway and an N-formyl-L-leucine group ester linked to the 5-hydroxyl group of the back bone. The composts of the lipstatin are ultimately from linoleic acid, octanoic acid, and L-leucine.
The 22 carbon β-lactone moiety is derived from Claisen condensation between 3-hydroxytetradeca-5,8-dienyl-CoA derived from linoleic acid and hexyl-malonyl-ACP derived from octanoic acid.Linoleic acid is first attached to CoA through some acyl-CoA synthetase homologue synthesized by lipstatin biosynthetic operons (Lst) and goes through two β-oxidaition to hydroxytetradeca-5,8-dienyl-CoA. 3’ hydroxyl group from solution H2O is added by enoyl reductase homologue followed by enoyl hydratase homologue. Octanoic acid is also attached to CoA through similar acyl-CoA synthetase homologue (LstC) to form octanoyl-CoA. Octanoyl-CoA is 2’ carboxylated and loaded to acyl carrier protein (ACP) borrowed from primary metabolism to form hexyl-malonyl-ACP.
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Wikipedia