We report the synthesis of a series of oligo-�-peptides with elongated charged side chains and characterization of their secondary structure. As analogues of natural peptides, �-peptides are an important class of artificial foldamers that can fold into helices or sheets. Recently, our group reported for the first time that water-soluble a-polypeptide electrolytes can readily form an ultra-stable helical structure by situating charges distally from the polypeptide backbone. We tested whether this strategy could be applied to �-helical peptide analogues. Starting from L-tyrosine, we synthesized an Fmoc-protected �-amino acid with a Boc-protected amine group on the side chain 13 s-bonds away from the backbone. Through solid phase synthesis, we obtained a series of oligo-�-peptides with different lengths (DP = 4, 5, 6). The structures and purities were confirmed by MALDI-TOF and HPLC. Interesting secondary structures and their relationships to the peptide lengths were revealed by CD and NMR analysis.

Synthesis of water soluble ionic �-peptides with helical structure

246th National Meeting (2013)

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