Synthesis of oligosaccharides on polymer supports. Part I. 6-O-(p-vinylbenzoyl) derivatives of glucopyranose and their copolymers with styrene

Solid-Phase Oligosaccharide Synthesis and Combinatorial Carbohydrate Libraries

“…The polymer support was created by copolymerization of styrene with a sugar monomer equipped with a polymerizable O-protecting group. 28 This linear, noncrosslinked, soluble polymer allowed for glycosylation reactions in homogeneous solution but was readily precipitated to facilitate purification. For the first time the glycosyl donor was attached to the support and reacted with an excess of solution-based acceptor.…”

Organic Synthesis on Soluble Polymer Supports: Liquid-Phase Methodologies

“…Initial attempts to develop a method of liquid-phase oligosaccharide synthesis created a soluble polystyrene support bearing the first sugar unit by copolymerizing one of four 6- O -vinylbenzoylglucopyranose derivatives with styrene (Figure ) . Polymers of varying saccharide content were obtained and exhibited solubilities similar to polystyrene.…”

Chemoenzymatic Solution- and Solid-Phase Synthesis ofO-Glycopeptides of the Mucin Domain of MAdCAM-1. A General Route toO-LacNAc,O-Sialyl-LacNAc, andO-Sialyl-Lewis-X Peptides

“…The excess equivalents needed for quantitative coupling cannot be recycled without risking the incorporation of partially racemized material into the next reaction. Although some progress has been made in the chemical synthesis of oligosaccharides on solid phase, these methods were applied only occasionally to glycopeptide synthesis. − One reason for the lack of a general method for on-resin carbohydrate synthesis is the necessity to differentiate numerous protecting groups of the supported glycopeptides, a methodology which can be omitted if enzymatic protocols are used. Glycosyltransferases have shown to be versatile tools in oligosaccharide synthesis, especially in the synthesis of naturally occurring oligosaccharides.…”