Glycoconjugates, oligosaccharides

The important role saccharides play in biology, especially in recognition processes, led researchers to work on the development of multivalent so-called neo-glycoconjugates the numerous biological roles of cell surface oligosaccharides... 

J. P. Thompson and C.-L. Schengrund, Oligosaccharide-derivatized dendrimers Defined multivalent inhibitors of the adherence of the cholera toxin B subunit and the heat labile enterotoxin of E. coli to GM1, Glycoconjug. J., 14 (1997) 837-845. 

Biotinylated oligosaccharides are convenient probes of carbohydrate interactions, because the biotin label can be captured or detected using an avidin or streptavidin derivative. For instance, immobilized streptavidin can be used to purify glycoconjugates that have been labeled... 

Manger, I.D., Rademacher, T.W., and Dwek, R.A. (1992) 1-N-Glycyl P-oligosaccharide derivatives as stable intermediates for the formation of glycoconjugate probes. Biochemistry 31, 10724-10732. 

O Shannessy, D.J., and Wilchek, M. (1990) Immobilization of glycoconjugates by their oligosaccharides Use of hydrazido-derivatized matrices. Anal. Biochem. 191, 1-8. 

Application to target/total synthesis (oligosaccharides, glycoconjugates, natural products)... 

This review covers the recent advances in the use of O-glycosyl imidates in oligosaccharide and glycoconjugate synthesis, with emphasis on literature published between 1999 and 2006. However, because of the large volume of work in this area, only the most representative applications will be presented. One can refer to the similar preceding review [381] published in 2000 and another quite comprehensive review [375] on trichloroacetimidate method published in 1994 for earlier application of glycosyl trichloroacetimidates. Trifluoroacetimidate method will be discussed separately in this review in the light of its less popularity in carbohydrate chemistry. 

The trichloroacetimidate method has also found wide applications in the synthesis of various complex oligosaccharides. In the course of the development of chemically defined glycoconjugate vaccines against shigellosis, a decasaccharide, corresponding to two consecutive repeating units of the O-specifk polysaccharide of Shigella... 

The Fischer- Helferich method, as a direct anomeric-oxygen replacement reaction (Scheme 1, path A), has been very successfully applied for syntheses of simple alkyl glycosides. However, because of its reversibility, it has not gained general importance in the synthesis of complex oligosaccharides and glycoconjugates (1). 

The Glycal Assembly Method on Solid Supports Synthesis of Oligosaccharides and Glycoconjugates... 

Oligosaccharides and glycoconjugates in living cells often exist as closely related mixtures. Their isolation from natural sources in homogeneous form is therefore very difficult, involving tedious purification and difficult characterization. This sequence of steps tends to result in low yields. This difficult situation presents chemical synthesis with a major opportunity to positively affect progress in the biochemical understanding of the processes described above.4... 

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... 

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