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2 0 0 0 OA Sanglifehrins A, B, C and D, Novel Cyclophilin-binding Compounds Isolated from Streptomyces sp. A92-308110

著者
THEODOR FEHR JÖRG KALLEN LUKAS OBERER JEAN-JACQUES SANGLIER WOLFGANG SCHILLING
出版者
JAPAN ANTIBIOTICS RESEARCH ASSOCIATION
雑誌
The Journal of Antibiotics (ISSN:00218820)
巻号頁・発行日
vol.52, no.5, pp.474-479, 1999-05-25 (Released:2008-09-19)
参考文献数
4
被引用文献数
70 87
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.

1 0 0 0 OA Sanglifehrins A, B, C and D, Novel Cyclophilin-binding Compounds Isolated from Streptomyces sp. A92-308110

著者
JEAN-JACQUES SANGLIER VALERIE QUESNIAUX THEODOR FEHR HANS HOFMANN MARION MAHNKE KLAUS MEMMERT WALTER SCHULER GERHARD ZENKE LILIANE GSCHWIND CLAUDINE MAURER WOLFGANG SCHILLING
出版者
JAPAN ANTIBIOTICS RESEARCH ASSOCIATION
雑誌
The Journal of Antibiotics (ISSN:00218820)
巻号頁・発行日
vol.52, no.5, pp.466-473, 1999-05-25 (Released:2008-09-19)
参考文献数
20
被引用文献数
52 112 105
A novel class of macrolides for which the name sanglifehrins is proposed, has been discovered from actinomycete strains based on their high affinity binding for cyclophilin A (CypA), an immunophilin originally identified as a cytosolic protein binding cyclosporin A (CsA). The sanglifehrins were produced by Streptomyces sp. A92-308110. They were isolated and purified by extraction and several chromatographic, activity-guided steps. Sanglifehrins A and B exhibit a 10-20 fold higher affinity for CypA than CsA, whereas the affinity of sanglifehrins C and D for CypA is comparable to that of CsA. Sanglifehrins exhibit a lower immunosuppressive activity than CsA when tested in the mixed lymphocyte reaction. Their in vitro activity indicates that they belong to a novel class of immunosuppressants.