Oligosaccharides and glycoconjugates

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 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... 

J. E. Heidlas, K. W. Williams, and G. M. Whitesides, Nucleoside phosphate sugars Syntheses on practical scales for use as reagents in the enzymatic preparation of oligosaccharides and glycoconjugates, Acc. Chem. Res. 25 307 (1992). 

Both transferases from the Leloir and non-Leloir pathways have been employed for the in vitro synthesis of oligosaccharides and glycoconjugates. Glycosidases have also been exploited for synthesis. The function of glycosidases in vivo is to cleave glycosidic bonds,... 

N. K. Kochetkov, Solid-phase synthesis of oligosaccharides and glycoconjugates, Russian Chem. Rev., 69 (2000) 795-820. 

J. W. Gillard Development of novel antiviral nucleoside analogues S. J. Danishefsky Glycals in the synthesis of oligosaccharides and glycoconjugates... 

S. Aduru and B. T. Chait, Cf-252 plasma desorption mass spectrometry of oligosaccharides and glycoconjugates—control of ionization and fragmentation, Anal Chem., 63 (1991) 1621-1625. 

---