Abstract
A cyclic hexapeptide, cyclo(Pro-Sar-Sar) 2, which consists of N-substituted amino acids only was synthesized, and its solution conformation was investigated by n.m.r. spectroscopy. Seven different C 2-symmetric conformations were detected, which were distinguishable from each other on the n.m.r. time scale. This is due to the cis/trans isomerization of N-substituted peptide bonds. Allowed C 2-symmetric conformations were computed on the basis of a hard-sphere model. Some conformations detected in n.m.r. spectra were not allowed in the calculation. This disagreement suggests that some asymmetric conformations with regard to the single bond rotation are averaged out due to a rapid rotation on the n.m.r. time scale. These points indicate that the molecule of cyclo (Pro-Sar-Sar) 2 is very flexible
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