Synthesis and antigenic properties of sugar-polypeptide conjugates

Synthesis of Side-Chain Modified Polypeptides

“…In seminal work, Sela's and Rude's laboratories prepared the first saccharide SCM NCAs, O-linked glycosylated serine NCAs ( Figure 5A), 40,41 in an effort to study how addition of sugars to polypeptides would affect their immunological properties.…”

Transition Metals for the Synthesis of Glycopolymers and Glycopolypeptides

“…Rüde prepared the first O ‐glycosylated N ‐carboxy anhydride (NCA) by the use of modified Koenig‐Knorr glycosidation conditions21 to study immunological properties of glycopolypeptides 16. After several years, Okada’s group synthesized glycoamino acid building blocks by Rüde’s method and studied synthesis of glycopolypeptides 22…”

“…The third, and more advantageous, method of glycopolymer syntheses is the polymerization of a carbohydrate residue, with a pendant polymerizable functional group, under suitable conditions, to afford good glycan density, as well as periodicity (Method 3, Figure 3). For example, glycopolymers can be synthesized by a free radical polymerization of acryloyl and acrylamido glycosides,15a and glycopolypeptides can be obtained by the ring‐opening polymerization15b–e of N ‐carboxyanhydride (NCA)16 containing sugar‐amino acid hybrid molecules.…”

Recent advances in glycopolypeptide synthesis

“…103 Acetobromoglucose and Ncarboxybenzyl-L-serine benzyl ester were reacted together in a mercuric cyanide mediated Koenigs-Knorr reaction. (Figure 11) After removal of the amino acid protecting groups, β-Dglucopyranosyl-L-serine NCA was prepared by the Leuchs method in 15 to 40% yield.…”