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Cyclosporin A, ein immunsuppressiv wirksamer Peptidmetabolit aus Trichoderma polysporum (L INK ex P ERS .) Rifai
Author(s) -
Rüegger Artur,
Kuhn Max,
Lichti Heinz,
Loosli HansRudolf,
Huguenin René,
Quiquerez Charles,
von Wartburg Albert
Publication year - 1976
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19760590412
Subject(s) - chemistry , edman degradation , stereochemistry , oligopeptide , hydrolysis , peptide , metabolite , antifungal , amino acid , cyclic peptide , biochemistry , peptide sequence , microbiology and biotechnology , biology , gene
Cyclosporin A, a Peptide Metabolite from Trichoderma polysporum (L INK ex P ERS .) Rifai , with a remarkable immunosuppressive activity Two antifungal metabolites, cyclosporins A and C, were isolated from a strain of Trichoderma polysporum (L INK ex P ERS .) Rifai . Cyclosporin A, the main component, has the molecular formula C 62 H 111 N 11 O 12 as deduced by NMR. and mass spectra. Hydrolytic cleavage of cyclosporin A furnished 11 amino acids as fragments, among them an artefact of a new C 9 ‐amino acid. The amino acid sequence was determined by Edman degradation of iso‐cyclosporin A, a basic rearrangement product formed from cyclosporin A by N , O ‐acyl migration. In an independent investigation an X‐ray analysis of the iodo derivative 10 was performed (see the following paper). On the basis of the chemical, spectroscopic and crystallographic evidence the complete structure of cyclosporin A was elucidated as the neutral cyclic oligopeptide 1 . Cyclosporin A and C show remarkable immunosuppressive and antiphlogistic activities in several pharmacological models.