Preparation of glycoprotein models: Pendant-type oligosaccharide polymers

  • Nishimura S
  • Furuike T
  • Matsuoka K
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Abstract

This chapter reviews advances in polymerizable glycosides that are useful for the preparation of macromolecules having pendant-type carbohydrates. Synthetic glycoconjugates have gained interest, both as convenient tools for investigating the biological roles of natural glycoconjugates and as a new class of biomaterials in medical science. Progress in the chemical syntheses of complex oligosaccharides of glycoconjugates has considerably enhanced the ability to design and synthesize not only naturally occurring bioactive oligosaccharides, but simplified biomimetic molecules for investigating the nature of cell-surface receptors that specifically interact with sugar molecules. Although a number of polymerizable glycosides are available as monomers for the preparation of carbohydrate-carrying macromolecules, judicious consideration must be given for establishment of sophisticated methods for syntheses of the functional glycosides that have, in addition to the polymerizable functions, appropriate spacer-arm moieties to provide the flexibility of carbohydrate branches. The trimethylsilyltrifluoromethane sulfonate (TMSOTf) method is one of the most efficient and versatile procedures for chemical conversion of oligosaccharides containing a GlcpNAc residue at the reducing end to glycosides through the oxazoline derivatives. © 1994, Elsevier Inc. All rights reserved.

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