Sanglifehrins A, B, C and D, Novel Cyclophilin-binding Compounds Isolated from Streptomyces sp. A92-308110 II. Structure Elucidation, Stereochemistry and Physico-chemical Properties

THEODOR FEHR; JÖRG KALLEN; LUKAS OBERER; JEAN-JACQUES SANGLIER; WOLFGANG SCHILLING

doi:10.7164/antibiotics.52.474

Sanglifehrins A, B, C and D, Novel Cyclophilin-binding Compounds Isolated from Streptomyces sp. A92-308110

II. Structure Elucidation, Stereochemistry and Physico-chemical Properties

THEODOR FEHR, JÖRG KALLEN, LUKAS OBERER, JEAN-JACQUES SANGLIER, WOLFGANG SCHILLING

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JOURNAL FREE ACCESS

1999 Volume 52 Issue 5 Pages 474-479

DOI https://doi.org/10.7164/antibiotics.52.474

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Abstract

A novel class of macrolides, the sanglifehrins, was discovered by screening of actinomycete strains with a cyclophilin-binding assay. The chemical structures and absolute stereochemistries of the sanglifehrins A, B, C and D were determined unambiguously by NMR-techniques and by X-ray crystallography of the complex with cyclophilin A. Sanglifehrin A consists of a 22-membered macrocycle containing a tripeptide subunit and features in position 23 a chain of nine carbon atoms bearing a spirocyclic substituent. Sanglifehrins A and B are genuine metabolites whereas sanglifehrins C and D are artefacts.

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