Efficient synthesis of carbopeptoid oligomers: insight into mimicry of β-peptide

Abstract

The ready access to a new class of carbohydrate mimetics was demonstrated by the synthesis of tetrameric carbopeptoids, in which glycosidic bonds were replaced with amide linkages. We herein describe the detailed synthetis method of β(1→2)- and β(1→6)-linked carbopeptoids starting from each d-glucosamine and d-glucose derivative. The building blocks were polymerized using BOP reagent and DIEA to form a homooligomer. These produced carbopeptoids are resistant to glycosidases and have interesting biological activity. With conformational analysis by molecular modeling calculation, β(1→2)-linked decamer showed a typical 16-helix form as a mimic of β-peptide. Therefore, our polysaccharide analogues have potential as peptide foldamers.