Synthesis and CD Spectra of β2-(3-Aza-peptides)

Abstract

A symposium report. New types of peptides, b2-(3-aza-peptides), were prepd. from the natural a-amino acids via an amination reaction in the presence of a strong coupling reagent. Synthesis of the di- and tripeptide was achieved with good yields and negligible epimerization using HATU in CH2Cl2 or in DMF. Subsequent coupling and deprotection gave the b2-3-azahexapeptide in reasonable yield. The CD spectra of the tripeptides have a pattern similar to that of hexapeptides, indicating that oligomers derived from as little as three b2-3-aza-amino acids might already adopt a secondary structure. In contrast, the CD spectra of the debenzylated b2-3-aza-peptides are similar to that obtained for the b2-peptide. [on SciFinder (R)]