Oligosaccharides chemoenzymatic synthesis

Chemoenzymatic carbohydrate synthesis has been emerging as an extremely powerful tool to obtain complex oligosaccharides. Chemoenzymatic synthesis has many potential advantages, of which the most significant ones are probably that it offers perfect stereoselectivity and renders the tedious work of synthesizing various selectively protected monosaccharide units unnecessary. It also makes the most difficult glycosylation reactions seem easy (86). Chemoenzymatic synthesis of oligosaccharides is out of the scope of this chapter, but it was the topic of many excellent reviews (73,87-89). 

Hanson S, Best M, Bryan MC, Wong CH. Chemoenzymatic synthesis of oligosaccharides and glycoproteins. Trends Biochem. 

Schmidt D, Sauerbrei B, Thiem J. Chemoenzymatic synthesis of sialyl oligosaccharides with sialidases employing transglycosylation methodology. J. Org. Chem. 2000 65 8518-8526. 

DeAngelis PL, Oatman LC, Gay DF. Rapid chemoenzymatic synthesis of monodisperse hyaluronan oligosaccharides with immobilized enzyme reactors. J. Biol. Chem. 2003 278 35199-35203. 

Kondo, H, Ichikawa, Y, Wong, C-H, (i-Sialyl phosphite and phosphoramidite synthesis and application to the chemoenzymatic synthesis of CMP-sialic acid and sialyl oligosaccharides, J. Am. Chem. Soc., 114, 8748-8750, 1992. 

Glycosyltransferases Chemoenzymatic synthesis Oligosaccharide Glycoconjugate Carbohydrate synthesis... 

Cyclodextrins (CDs) have the ability to include the hydrophobic area of a compound, and the formed complex becomes soluble in water due to hydroxyl groups orientated on the surface of CDs. Thus, it was proposed that CDs would have similar properties as surfactants in enzymatic glycosylations. Nishimura etuL studied the utility of simple CDs for the synthesis of neoglycolipids using glycosyltransferase. In this approach, the authors attempted to use cell-media synthesis, which was named cellular-chemoenzymatic synthesis, as a triple-factor combination method, to construct oligosaccharide easily. Three types of CD, a-CD, /3-CD, and... 

The DeAngelis laboratory has developed the chemoenzymatic synthesis of monodisperse GAG oligosaccharides using single-action mutants. Potential medical applications for HA oligosaccharides (n = -3-10) include killing... 

Becker, H. R, A. Thellend, A. Piffeteau, and A. Vidal-Cros. 2006. Chemoenzymatic synthesis of stable isotope labelled UDP-N-[ H]-acetyl-glucosamine and [ H]-acetyl-chito-oligosaccharides. Glycoconj. J. 23 6S1-692. 

ChemoenzymatiC Synthesis. Original oligosaccharides bifunctional-ized with fluorescent entities were synthetized in the presence of a mutant of Humicola insolens endoglucanase (318). Hemithiocellodextrins with degree of polymerization from 4 to 14 were synthetized in the presence of a cellulase in buffer/organic solvent (319). 

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