Recent progress in the field of glycopeptide synthesis

Abstract

Glycosylation is a common post‐translational modification of proteins. Although its significance in biological system is well recognized, approaches to analyze carbohydrate function are limited. This is because of difficulty in obtaining homogeneous glycoproteins from natural sources. Due to the progress of the carbohydrate and peptide chemistry, syntheses of various homogeneous glycopeptides and glycoproteins, which are suitable for biological studies, have been achieved by chemical means. In this review, we briefly summarize recent advances in the field of glycopeptide synthesis after 1999. © 2007 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 88: 308–324, 2007. This article was originally published online as an accepted preprint. The ‘Published Online’ date corresponds to the preprint version. You can request a copy of the preprint by emailing the Biopolymers editorial office at biopolymers@wiley.com

Semisynthesis of a Homogeneous Glycoprotein Enzyme: Ribonuclease C: Part 2

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The synthesis of homogeneously glycosylated glycoproteins [1][2][3][4][5][6][7] and their analogues [8,9] provides a novel approach to study the importance of the carbohydrate moieties for the functions of therapeutic glycoproteins. These efforts were initially stimulated by the need to produce defined glycoforms for such investigations, and this research has gained further momentum by the evidence that individual glycoforms [10] can have distinctly different functions.

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Total Synthesis of Glycosylated Proteins

“…The chemical synthesis of glycoproteins requires the ability to prepare glycosylated peptide fragments efficiently [18, 19]. Peptide synthesis efforts typically rely on solid-phase peptide synthesis (SPPS) [20], a process which allows for the efficient assembly of peptide fragments comprising up to 50 amino acid residues.…”

Expressed protein ligation: a resourceful tool to study protein structure and function

“…Recent advances in the chemical synthesis of glycopeptides has allowed for the first time a reliable way to obtain homogeneous glycopeptides or glycoproteins (see ref. [116] for a recent review).…”