Cu-Catalyzed Formation of Triazole-Linked Glycoamino Acids and Application in Chemoenzymatic Peptide Synthesis

Abstract

Novel stable triazole-linked glycoamino acids have been prepared, with the heterocyclic moiety being established by efficient Cu-mediated cycloaddition between the corresponding azido and acetylene moieties. Selected reactions were scaled up and successfully subjected to chemoenzymatic peptide-coupling reactions involving the proteolytic enzyme alcalase, resulting in several glycosylated di- and tripeptide structures. Since chemoenzymatic approaches have several advantages over chemical peptide coupling, especially concerning large-scale peptide synthesis, these results may be regarded as initial steps in the direction of production via fully chemoenzymatic peptide synthesis.