Glycoside hydrolases, a widely distributed group of enzymes, cleave glycosidic bonds in glycosides, glycan and glycoconiugates, and they can play roles in the development of biofuels and in desease research. Glycosidases also participate in a broad range of biological processes including the virulence of pneumococci, which cause a number of serious diseases that are responsible for millions of deaths annually [1]. Although these enzymes belong to the class of hydrolases, they can also synthesize glycosidic bond through the transglycosylation or reverse hydrolysis reaction.
The enzyme β-galactosidase (EC 3.2.1.23), which is usually hydrolyzing lactose to the monosaccharides like D-glucose and D-galactose, may also catalyse the formation of galacto-oligosaccharides [2,3]. In the synthesis of biologically active glycosides via enzymatic systems are still rare in literature. Indeed, the enzyme systems, the frequently observed low yields, the stringent specificities or the lack of an available catalyst still often favour chemical systems. In view of the often long-winded protection stages required for most chemical glycosylations, hovewer, the use of enzyme-catalysed one step systems is clearly an attractive proposition. Furthermore, enzymatic methods of glycosylation seem to be promising as a means of synthesizing unstable glycosides, because they can be carried out under mild conditions with no accompanying decomposition of the starting materials or products [4]. The synthesis of novel 2-deoxygalactosides is interesting because of their important role in several biological processes [5]. Therefore, to study biological activity, it is essential to elucidate the structure of the products.Glycosidases are capable of catalyzing glycosidic linkages with absolute stereoselectivity of the anomeric center.
We report an efficient synthesis of alkyl and aryl β-D-2-deoxygalactopyranosides derivatives in presence of β-galactosidases .

Acknowledgement

Research studies part-financed by the European Union within the European Regional Development Fund (POIG. 01.01.02-14-102/09).

References

[1] Abbott DW, Macauley MS, Vocadlo DJ, Boraston AB. 2009. J Biol Chem., 17  (2009), 11676; [2] K.C. Nicolaou, K. Chibale, Tetrahedron,  53 (1997), 8751; [3] Vic, G.; Hastings, J.; Crout, D.H.G. Tetrahedron Asymmetry, 7 (1996), 1973; [4] Crout, D. H. G.; Vic, G. Curr. Opin. Chem. Biol., 2 (1998), 98; [5] A. Trincone, E.Pagnotta, Biocatalysis and Biotransformation, 21 (2003), 17.

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