Synthesis of Oligosaccharide

These methods are usually applicable only to the reducing oligosaccharides, i.e., those having an unsubstituted hemiacetal grouping, since most isomerizations involve the reducing group. 

Alkaline Rearrangement, The reducing disaccharides isomerize in the presence of alkali to give a mixture of three sugars which consist of the two 

Glycal Synthesis, This method depends upon the preparation of a glycal (which has a doul)le bond between carbons 1 and 2 of the reducing residue 

Anomeric Rearrangement The transformation of certain glycosides from the to the a-configuration by the action of stannic chloride or titanium tetrachloride was observed by Pacsu 15), Recently this transformation has been applied to the oligosaccharides, effecting the synthesis of isomaltose from gentiobiose (see Isomaltose). 

---

Bundle, D. R. Synthesis of Oligosaccharides Related to Bacterial O-Anligens. 154, 1-37 (1990). 

Chemical synthesis of oligosaccharides related to arabinogalactan-proteins (agps) J.F. Valdor and W.Mackie... 

Moracci, M., Cobucci-Ponzano, B., Perugino, G. et al. (2005) Recent developments in the synthesis of oligosaccharides by hyperthermophilic glycosidases, in Handbook of Carbohydrate Engineering (ed. K.J. Yarema), CRC Press LLC, Boca Raton, FL, pp. 587-612. 

Murata, T. and Usui, T. (2006) Enzymatic synthesis of oligosaccharides and neoglycoconjugates. Bioscience, Biotechnology, and Biochemistry, 70, 1049-1059. 

Trincone, A. and Giordano, A. (2006) Glycosyl hydrolases and glycosyltransferases in the synthesis of oligosaccharides. Current Organic Chemistry, 10, 1163-1193. 

Rabbani, S., Schwardt, O. and Ernst, B. (2006) Glycosyltransferases an efficient tool for the enzymatic synthesis of oligosaccharides and derivatives as well as mimetics thereof. Chimia, 60, 23-27. 

Chen, X., Fang, J., Zhang, J.etal. (2001) Sugar nucleotide regeneration beads (superbeads) a versatile tool for the practical synthesis of oligosaccharides. Journal of the American Chemical Society, 123, 2081-2082. 

This report surveys new routes for the synthesis of oligosaccharides, with emphasis on enzymatic reactions, since they offer unique properties, proceeding highly regio-and stereo-selectively in water solution, and generally afford high yields. Summarized... 

M. Remaud-Simeon, A. Lopez-Munguia, V. Pelenc, F. Paul, and P. Monsan, Production and use of glucosyltransferases from Leuconostoc mesenteroides NRRL B-1299 for the synthesis of oligosaccharides containing a-(l >2) linkages, Appl. Biochem. Biotechnol., 44 (1994) 101-117. 

T. Murata and T. Usui, Enzymatic synthesis of oligosaccharides and neoglyco-conjugates, Biosci. Biotechnol. Biochem., 70 (2006) 1049-1059. 

---