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Peptide Conformation, IX Conformational Studies on Cyclotripeptides Containing N‐Benzyl‐Glycine
Author(s) -
Kessler Horst,
Krämer Peter,
Krack Gerhard
Publication year - 1980
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198000071
Subject(s) - tripeptide , chemistry , nuclear magnetic resonance spectroscopy , peptide , stereochemistry , cyclic peptide , peptide conformation , crystallography , peptide bond , two dimensional nuclear magnetic resonance spectroscopy , crystal structure , biochemistry
Synthesis and NMR spectra of the cyclic tripeptides of the general structure cyclo[Pro x Bzl.Gly 3‐x ] (x = 0–2; Bzl.Gly. = N‐Benzylglycyl) are reported. Two slowly interconverting conformations of these tripeptides containing only cis peptide bonds have been observed in solution by NMR spectroscopy. Structural proof and assignments to a flexible boat conformation and a rigid crown conformation, respectively, have been achieved by interpretation of the NMR parameters and the correlation with the crystal structure of one compound. The conformational behaviour of cyclic tripeptides is discussed.