Synthesis of glycopeptides and glycopeptide conjugates

Abstract

Synthetic glycopeptides are of key importance for unraveling the complexities of glycobiology. In this Review, the key approaches towards synthetic well-defined glycopeptides and glycopeptide conjugates are described.

Glycopolymers against pathogen infection

“…This review will exclusively focus on glycopolymers as multivalent glycan mimetics composed of a synthetic macromolecular or polymeric scaffold presenting carbohydrate motifs in the side chain. This is in contrast to similar macromolecular glycoconjugates such as glycopeptides, [16][17][18][19] glycodendrimers, 20,21 glycan-functionalized nanomaterials [22][23][24] or combinations thereof [25][26][27] (Fig. 2).…”

Merging Solid‐Phase Peptide Synthesis and Automated Glycan Assembly to Prepare Lipid‐Peptide‐Glycan Chimeras

“…Glycopeptides are synthesized by incorporating glycosylated amino acid residues in the course of solid-phase peptide synthesis (SPPS). [26,27] In addition to inherent limitations associated with the complex and lengthy synthesis of these building blocks (BBs), poor conversion, racemization, and β-elimination render this method very case-dependent. [27] Currently, glycan assembly on resin-bound peptides is state-of-the-art (Scheme 1B).…”

“…[26,27] In addition to inherent limitations associated with the complex and lengthy synthesis of these building blocks (BBs), poor conversion, racemization, and β-elimination render this method very case-dependent. [27] Currently, glycan assembly on resin-bound peptides is state-of-the-art (Scheme 1B). Few examples have been reported due to the need to subject the peptide to harsh glycosylation conditions.…”

Mining the Immunopeptidome for Antigenic Peptides in Cancer

“…Other glycosylated immunopeptides have also been investigated as vaccines, tumor-selective antibodies, CAR T cells, nanoparticles, and DC therapy [ 78 , 79 , 80 , 81 , 82 , 83 , 84 , 85 , 86 , 87 , 88 ]. Critical to this effect is knowledge of the structure of glycoproteins for their synthesis and antibody binding properties and their surface localization and occurrence in the immunopeptidome [ 89 , 90 , 91 , 92 , 93 , 94 , 95 , 96 , 97 , 98 , 99 , 100 ]. Interestingly, MHC-I also undergoes glycosylation, which must be taken into account for antigen presentation [ 101 ].…”