Oligosaccharide solid-phase synthesis applications

The application of solid-phase synthesis and automation has revolutionized much of the chemical and biochemical research related to peptides and nucleic acids.5 Thus, it is likely that successful methods to synthesize oligosaccharides and glycoconjugates... 

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. 

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. 

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. 

A tandem RCM-cleavable linker for application to the solid-phase synthesis of oligosaccharides has recently been reported [136]. The system makes use of a tri-ene linker system, resulting in the fact that the RCM regenerates the active Ru catalyst without the need for an alkene co-factor. The application of this hnker was demonstrated in the hberation of a cyclopent-2-enyl mannoside from the solid support. Subsequent isomerization to the vinyl ether glycoside led to the depro-tected mannose after iodine treatment. The basic principle of the approach is out-hned in Scheme 52. 

Application of Unique Glycosylation Methods in Solution to Solid-Phase Synthesis of Oligosaccharides... 

Oligosaccharides.—An edited series on the methods and the applications of solid-phase syntheses includes a section on the solid-phase synthesis of oligosaccharides. ... 

Knerr L, Schmidt RR. Application of a ring closing metathesis based linker to the solid phase synthesis of oligosaccharides. Synlett 1999 1802-1804. 

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. 

The Sulfoxide Glycosylation Method and its Application to Solid-Phase Oligosaccharide Synthesis and the Generation of Combinatorial Libraries... 

Scheme 4.12 Application of CPG support in solid-phase oligosaccharide synthesis using glycosyl trichloroacetimidates.

Solid-Phase Oligosaccharide Chemistry and Its Application to Library Synthesis... 

Randolph JT, McClure KF, Danishefsky SJ, Major simplifications in oligosaccharide syntheses arising from a solid-phase based method An application to the synthesis of the Lewis b Antigen, J. Am. Chem. Soc., 117 5712-5719, 1995. 

---