Sanglifehrins A, B, C and D, novel cyclophilin-binding compounds isolated from Streptomyces sp A92-308110 -: II.: Structure elucidation, stereochemistry and physico-chemical properties

被引:97
作者
Fehr, T [1 ]
Kallen, J [1 ]
Oberer, L [1 ]
Sanglier, JJ [1 ]
Schilling, W [1 ]
机构
[1] Novartis Pharma Inc, Res, Dept Core Technol, CH-4002 Basel, Switzerland
关键词
D O I
10.7164/antibiotics.52.474
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
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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页码:474 / 479
页数:6
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