Glycosyltransferases in oligosaccharide synthesis

X Qian, K Sujino, RM Ratcliffe, MM Palcic - Glycochemistry, 2001 - taylorfrancis.com
X Qian, K Sujino, RM Ratcliffe, MM Palcic
Glycochemistry, 2001taylorfrancis.com
I. INTRODUCTION Recent demonstrations that oligosaccharides play important roles in
diverse biological events have resulted in renewed interest in the synthesis of
oligosaccharides and their analogs. The availability of such molecules can facilitate studies
on carbohydrate-protein recognition and help to elucidate molecular mechanisms of
oligosac-charide-mediated biological processes [1, 2] that could eventually lead to rationally
designed carbohydrate-based therapeutics [3, 4]. Despite many advances that have been …
I. INTRODUCTION Recent demonstrations that oligosaccharides play important roles in diverse biological events have resulted in renewed interest in the synthesis of oligosaccharides and their analogs. The availability of such molecules can facilitate studies on carbohydrate-protein recognition and help to elucidate molecular mechanisms of oligosac-charide-mediated biological processes [1,2] that could eventually lead to rationally designed carbohydrate-based therapeutics [3,4]. Despite many advances that have been made over the past decades, the chemical synthesis of oligosaccharides remains a challenge [5,6]. This is attributed to the inherent chemical difficulties presented by this class of molecules. Each monosaccharide carries at least three hydroxyl groups that must be protected and deprotected during synthesis.Also, glycosylation generates a new stereocenter at the anomeric carbon, and there are no general methods for the introduction of all types of glycosidic linkage in a manner that is both stereo-controlled and high yielding. The chemical synthesis of oligosaccharides is therefore very time-consuming and requires specialized expertise. The synthesis of oligosac-charide analogs containing modified sugars is an even more complex task than the preparation of natural structures.Almost twice as many steps are usually required for analog synthesis and the steps are more difficult, since most chemical protocols in the literature have been optimized for natural sugars.
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