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Solution NMR Structures of the Polyene Macrolide Antibiotic Filipin III

Solution NMR Structures of the Polyene Macrolide Antibiotic Filipin III

L Volpon, J Lancelin

FEBS Lett. 2000 Jul 28;478(1-2):137-40.

PMID: 10922485

Abstract:

The solution structure of filipin III, an antifungal polyene macrolide biosynthesized by Streptomyces filipinensis and widely used for the detection and the quantitation of cholesterol in biomembranes, has been calculated with a set of geometrical restraints derived from 1H NMR in DMSO-d(6) at 25 degrees C. Filipin III appears as a rod-shaped molecule of 18 A length. Its amphiphilic structure is made of an all-syn 1,3-polyol motif, stabilized by intramolecular hydrogen bonds on one side, and a conjugated pentaene moiety on the other side of the molecule. The overall shape is comparable to cholesterol, and the molecular structure of filipin III affords a first molecular basis to the comprehensive understanding of the interactions possible in the filipin III-cholesterol complex which is still unknown at the atomic resolution.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP11078210	Filipin complex from Streptomyces filipinensis		11078-21-0	Price
AP480499	Filipin III from Streptomyces filipinensis		480-49-9	Price

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