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Neue Cyclopeptide aus Trichoderma polysporum (L INK EX P ERS .) R IFAI : Die Cyclosporine B, D und E
Author(s) -
Traber René,
Kuhn Max,
Loosli HansRudolf,
Pache Walter,
Von Wartburg Albert
Publication year - 1977
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.19770600513
Subject(s) - cyclosporins , chemistry , stereochemistry , oligopeptide , amino acid , biological activity , peptide , biochemistry , transplantation , medicine , surgery , in vitro
New Cyclopeptides from Trichoderma polysporum (L INK EX P ERS .) R IFAI : Cyclosporins B, D and E Cyclosporins represent a new group of biologically active metabolites produced by Trichoderma polysporum (L INK EX P ERS .) R IFAI and other fungi imperfecti. The structures of the main components, cyclosporins A ( 1 ) and C( 3 ) have been determined as neutral cyclic oligopeptides composed of 11 amino acids, among them a new C 9 ‐amino acid [2–4]. In addition, three minor metabolites, cyclosporins B, D and E, have now been isolated and characterized. Chemical investigation, spectroscopic evidence and X‐ray analysis led to the structural formulae of cyclosporins B (2) and D (4) . Both compounds have the same sequence of amino acids as cyclosporin A (1) , with the exception of L ‐α‐aminobutyric acid, replaced in cyclosporin B (2) by L ‐alanine and in cyclosporin D (4) by L ‐valine, respectively. Cyclosporins undergo a characteristic intramolecular N , O ‐acyl migration to furnish the corresponding basic isocompounds. The antifungal activities of cyclosporins are reported.