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Die Struktur von Cyclosporin C
Author(s) -
Traber René,
Kuhn Max,
Rüegger Artur,
Lichti Heinz,
Loosli HansRudolf,
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.19770600414
Subject(s) - chemistry , stereochemistry , intramolecular force , metabolite , hydrogen bond , nuclear magnetic resonance spectroscopy , oligopeptide , ring (chemistry) , molecule , peptide , biochemistry , organic chemistry
The Structure of Cyclosporin C The structure of cyclosporin C ( 2 ), a minor antifungal metabolite from Trichoderma polysporum (Link ex Pers.) R IFAI has been elucidated. Hydrolytic cleavage and spectroscopic evidence show that cyclosporin C is a neutral oligopeptide of 11 amino acids linked together in a 33‐membered ring. Cyclosporin C ( 2 ) differs from the main metabolite cyclosporin A ( 1 ) [2] [4] only by containing L‐threonine in the place of L‐α‐aminobutyric acid as has been shown by the conversion of 2 into 1 . 13 C‐NMR. spectra and study of molecular models suggest that cyclosporin C ( 2 ) has the same molecular conformation as 1 , which is best described as a twisted β‐pleated sheet held together in a conformationally stable form by intramolecular hydrogen bonding.