Folding types of dipeptides containing the diastereoisomeric cyclopropanic analogues of phenylalanine

Article abstract of DOI:10.1016/S0040-4039(97)10034-X

In order to consider the possible influence of the orientation of a side chain on the peptide backbone, we have studied the molecular structure of four (t)BuCO-Pro-c₃Phe-NHMe model dipeptides, where c₃Phe denotes each of the four diastereoisomeric 2,3-methanophenylalanines, by using IR and proton NMR experiments. All four derivatives are β-folded, but the folding type depends on the stereochemistry of the cyclopropane moiety.