Abstract
In a previous communication we reported the racemic synthesis of the cis peptide bond mimic α-benzyl-o-aminomethylphenylacetic acid and its incorporation in the cyclic somatostatin analoguesc[α(R andS)Bn-o-AMPA-Phe7-d-Trp8-Lys9-Thr10]. Since the epimeric peptides exhibit different binding affinities, we completed the structure-activity study with an asymmetric synthesis. A model for the solution conformation ofc[α(R andS)Bn-o-AMPA-Phe7-d-Trp8-Lys9-Thr10] is proposed on the basis of a 2D NMR study in CD3OH and restrained molecular dynamics.
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