Oligosaccharides polymer-supported synthesis

High selectivity and substrate specificity of glycosyl transferases make them valuable catalysts for special linkages in polymer-supported synthesis. There is, however, still a rather limited set of enzymes available to date, and the need to synthesize a variety of natural and non-natural oligosaccharides prevails. Particularly with regard to combinatorial approaches, chemical solid-phase oligosaccharide synthesis promises to meet the demands most effectively. 

Scheme 9.1 Comparison of one-phase and two-phase polymer-supported synthesis of oligosaccharides. Continued next page.

Scheme 9.2 Comparison of polymer-supported synthesis of oligosaccharides between the attachment of a polymer to a glycosyl donor and a glycosyl acceptor.

Scheme 9.3 Polymer-supported synthesis of oligosaccharides employing a hydrophobic handle attached to the growing chain in the last step of the synthetic sequence. The handle permits separation of the majority of failure sequences accumulated during the synthesis.

Frechet, J. M. J., Polymer-Supported Synthesis of Oligosaccharides, Chap. 8 in Polymer-Supported Reactions in Organic Synthesis, P. Hodge and D. C. Sherrington, eds., Wiley, New York, 1980b. 

In another report of polymer-supported synthesis of an oligosaccharide Cp2HfCl2-AgOTf was used for activation of glycosyl fluoride on a resin (Fig. 6) [12a]. 

Knerr L, Schmidt RR (2001) The Use of O-Gly-cosyl Trichloroacetimidates for the Polymer Supported Synthesis of Oligosaccharides. In Seeberger PH (ed) Solid Support Oligosaccha-... 

Krepinsky, J. J., Douglas, S. P. Polymer-supported synthesis of oligosaccharides. Carbohydrates in Chemistry and Biology 2000, 1,239-265. 

Further breakthroughs in the area of synthetic chemistry emerged with the development of organic synthesis on solid phase.223-226 As a consequence, the past decade has witnessed dramatic improvements in the area of solid phase-supported oligosaccharide synthesis.202,227-230 Polymer-supported synthesis is a very attractive techniques as it allows for rapid synthesis of oligosaccharide sequences without the... 

Osborn, H. M. and Khan, T. H. Recent developments in polymer supported synthesis of oligosaccharides and glycopeptides. Tetrahedron 55 lS07-lS50, 1999. 

Two major advances used to streamline the chemical synthesis of oligosaccharides are one-pot reactions (101) and polymer-supported synthesis (see Section 3.1.4) (102). 

The endoglycosidase, ceramide glycanase, is used to transfer an oligosaccharide group from a water-soluble polymer to ceramide. This enzymatic tool provides an efficient new method for polymer-supported synthesis of glycosphingolipids (119). 

Haase, W.-C. and Seeberger, P.H., Recent progress in polymer-supported synthesis of oligosaccharides... 

Krepinsky JJ, Douglas SP (2000) Polymer-supported synthesis of oligosaccharides. In Ernst B, Hart GW, Sinay P (eds) Carbohydrates in chemistry and biology, vol 1. Wiley-VCH, Weinheim, pp 239-265... 

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