Oligosaccharides automated solution-phase synthesis

These results demonstrate that O-glycosyl trichloroacetimidate-based oligosaccharide synthesis on solid support may eventually become a valuable alternative to solution-phase synthesis because useful experience is available for the selection of the polymer support and choice of the linker system and the glycosyl donor. Further standardization of the building blocks and the protective group pattern will finally provide the yields and the anomeric control in order to successfully plan automated syntheses of oligosaccharides also in a combinatorial manner. 

Automated Solution-Phase Oligosaccharide Synthesis and Carbohydrate Microarrays Development of Fluorous-Based Tools for Glycomics... 

An Automated Solution-phase Strategy for Oligosaccharide Synthesis... 

Scheme 8.8 Automated iterative solution-phase synthesis of oligosaccharides using fluorous solid-phase extraction (FSPE) to purify the growing oligosaccharide chain n grows by one after each coupling cycle.

In conclusion, compared with solution-phase synthesis, solid-phase enzymatic synthesis, generally, needs higher concentrations of enzyme, longer reaction times, and a large excess of donors. Although there is still room for improvement in terms of yields and scale-up of syntheses, in solid-phase synthesis purification procedures are straightforward so it is expected that this approach will open the route to automated oligosaccharide synthesis in the near future. 

Advances in solid-phase oligosaccharide synthesis led to the development of an automated platform that was first demonstrated by Peter Seeberger and coworkers in 2001 using a modified peptide synthesizer [38], Automated washing, deprotection, and glycosylation steps dramatically reduced the time and labor usually attributed to solution- and solid-phase synthesis of oligosaccharides. 

This chapter desribes the synthesis of glycosyl phosphates and their use as glycosylating agents. Their use in die construction of complex oligosaccharides, both in solution and on solid support, is presented. Their ease of synthesis in combination with their rapid activation have made them ideal glycosylating agents to be used for automated solid phase oligosaccharide synthesis. 

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