Abstract
Carbohydrates bearing both amino and carboxylate groups could be useful for expanding the repertoire of monomers used for building foldamers. In this paper, we give a full account of the synthesis of small hybrid γ/α-glycopeptides built with sugar γ-amino acids and l-alanine. The γ/α-glycopeptides obtained are the first featuring geminally β,β-disubstituted γ-amino acids in which the β-carbon is the pseudo anomeric carbon of a sugar ring. Their conformational properties were studied by NMR and solution infrared spectroscopy, circular dichroism and molecular dynamics simulation.
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