Post‐Modification of Amino Acids and Peptides for the Rapid Synthesis of C‐Glycoamino Acids and C‐Glycopeptides

Abstract

AbstractGlycoamino acids and glycoproteins, especially C‐glycoamino acids and C‐glycoproteins, attract tremendous interests in the realm of biology and chemistry due to their wide occurrence in natural products, excellent pharmacodynamic properties and dynamic stability. Compared with the traditional construction of the amino acid or the glycosyl moiety de novo, post‐modification of amino acids and peptides through direct glycosylation reactions constitute a powerful synthetic approach to attaining C‐glycoamino acids and C‐glycopeptides rapidly on account of the high step‐economy, broad functional group tolerance, and conservation of the chirality of the amino acid and glycosyl moieties. In this review, the recent developments in the synthesis of C‐glycoamino acids and C‐glycopeptides via the post‐modification of amino acids and peptides are summarized. Additionally, the important and representative examples, synthetic applications, and crucial mechanism investigations of these glycosylation reactions are also highlighted.