Oligosaccharides synthesis, automated solid phase

Carney CK.HarrySR,Sewell SL.WrightDW (2007) Detoxification Biominerals. 270 155-185 Castagner B, Seeberger PH (2007) Automated Solid Phase Oligosaccharide Synthesis. 278 289-309... 

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. 

Plante, O.J. Palmacci, E.R. Seebo-go-, P.H. (2001) Automated solid-phase synthesis of oligosaccharides. Science, 291, 1523-7. 

P. H. Seeberger Automated solid-phase synthesis of oligosaccharides to address biomedical problems... 

IV. Design of an Automated Solid-Phase Oligosaccharide Synthesis Strategy. 43... 

While no examples of automated solid-phase oligosaccharide synthesis had been reported until the work described here,2 automated oligosaccharide synthesis was predated by efficient methods for the synthesis of peptides3 and nucleic acids.4 Here we briefly discuss the general features of each method, with particular emphasis on the scale and efficiency of peptide and nucleic acid synthesis. 

The phytoalexin elicitor (PE) family of /1-D-glucans (Fig. 5) was selected as a target because these oligosaccharides had been synthesized previously in solution48,49 and on the solid support.50,51 It was our intention to investigate not only the application of glycosyl phosphates to automated solid-phase synthesis, but also to compare our method to the previously described reports of PE syntheses. 

We have developed an automated solid-phase approach for the chemical synthesis of oligosaccharides. Using an acceptor-bound solid-phase... 

Plante OJ, Palmacci ER, Seeberger PH (2001) Automated Solid-Phase Synthesis of Oligosaccharides Automated Solid-Phase Synthesis of Oligosaccharides. Science 291(5508) 1523 Progress Toward Poliomyehtis Eradication - India, January 2006-September (2007). 

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. 

FIGURE 12 Three platforms for automated solid-phase oligosaccharide synthesis, (a) Pressure-driven system, (b) Syringe pump-driven system, (c) HPLC pump-driven system. 

The automated solid-phase synthesis of oligosaccharides was first reported in 2001 [38], A peptide synthesizer was modified to enable solid-phase oligosaccharide synthesis. The synthesizer was equipped with a cooling system for low-temperature glycosylations. As in the case with other automated platforms, a combination of new technologies and synthetic methods were developed, and distinctive breakthroughs were achieved. Many state-of-the-art synthetic and analytical methods were adopted and adjusted over the years. The first decade of automated solid-phase oligosaccharide synthesis relied on the development of new methods to access complex structures (Fig. 7.3). 

For almost lOyears, automated solid-phase synthesis of oligosaccharides was performed on a modified peptide synthesizer. The first prototype of a specially made oligosaccharide synthesizer [39] features fully automated tailor-made syringe pump systems for accurate delivery of reagents. 

Hewitt MC, Snyder DA, Seeberger PH. Rapid synthesis of a glycosylphosphatidyUnositol-based malaria vaccine using automated solid-phase oligosaccharide synthesis. J. Am. Chem. Soc. 2002 124 13434-13436. 

Plante OJ, Pahnacci ER, Seeberger PH. Automated solid-phase synthesis of oligosaccharides. Science 2001 291 1523-1527. Seeberger PH, Werz DB. Synthesis and medical applications of ohgosaccharides. Nature 2007 446 1046-1051. 

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