Solid-phase oligosaccharide synthesis, technique

Most of the methodology used so far in solid-phase oligosaccharide synthesis was developed before the analytical techniques outlined above had been adopted. Now that a closer insight into the reactions has become available, one may expect exciting... 

Wu J, Guo Z. Cap and capture-release techniques applied to solid-phase oligosaccharide synthesis. J Org Chem 2006 71 7067-7070. 

Solid-phase organic synthesis (SPOS) is an established technique for generation of peptides,12 nucleotides,3 and more recently, carbohydrates (oligosaccharides).4-5 Supported syntheses of nonbiological oligomers6 16 and other small molecules17 21 have also been reported, reflecting the method s... 

Solution-phase oligosaccharide synthesis remains a slow process due to the need for iterative coupling and deprotection steps, with purification at each step along the way. To alleviate the need for repetitive purification events, solid-phase techniques have been developed.29,30 In solid-phase... 

In addition, a novel fluorous support has been developed recently as an alternative to traditional polymer supports and applied successfully to oligosaccharide synthesis in combination with the trichloroacetimidate method [541]. Each intermediate in the fluorous oligosaccharide synthesis [542,543] could be obtained by simple fluorous-organic solvent extraction, and the reactions could be monitored by TLC, NMR and MS, in contrast to solid-phase reactions. Moreover, the new liquid-phase technique is anticipated to be easily applicable to the large-scale synthesis. 

Many strategies have been and are still being developed to access oligosaccharides by chemical synthesis. This chapter focuses on recent developments in the automated solid-phase synthesis of oligosaccharides and emphasizes the recent advances of novel microreactor techniques for carbohydrate synthesis. 

This article gives an overview of the main technical aspects of solid-phase synthesis and reviews the application of this technique for the synthesis of oligopeptides and proteins, oligonucleotides, oligosaccharides, and small molecules. 

The isolation of products is sometimes a tedious and time-consuming procedure. Especially in the area of combinatorial synthesis of oligosaccharides either in solution or on solid-phase, a simple and effective isolation method is necessary because many compounds are handled at the same time. For instance, chromatography is a quite popular method for isolation of the products of organic synthesis. However, it is somewhat tedious and consumes a considerable amount of solvents, and optimization of the separation conditions sometimes requires much time. Therefore, techniques for pol)mier-supported purification such as catch-and-release ... 

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... 

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