Fucose is a deoxyhexose that is present in the L-configuration of many N- and O-linked oligosaccharide structures of membrane as well as soluble glycoproteins and glycolipids produced by mammalian cells. The fucose molecule is present in ABH blood group antigens and in some oligosaccharide structures. Fucose can be α1,2, α1,3, α1,4, and α1,6 linked to the glycans of glycoconjugates. This predisposes fucose to play a crucial role in biological recognition events, such as cell-cell and cell-matrix interactions [1]. For that reasons the chemical synthesis of fucosyl glycosides, especially an efficient method for the formation of 1,2-cis glycosidic bond is a challenging task. In this communication we report the novel and stereoselective fucosylation of using O-fucosyl N-allyl thiocarbamates as glycosyl donors. These compounds are readily obtained from anomerically-unprotected fucose by reaction with commercially available N-allyl isothiocyanate [2]. The application this method for the synthesis of alkyl glycosides, disaccharides, trisaccharides and glycoconjugates of fucose will be presented. This method was used in the synthesis 2’-O-α-L-fucopyranosyl-lactose important component of human milk.

Acknowledgments

Financial support from the Polish State Committee for Scientific Research (Grant No. 3 T09B11229) is gratefully acknowledged.

[1] Orczyk-Pawiłowicz M. Postepy Hig Med Dosw. 2007, 61, 240-252; Barili P.L., Catelani G., D’Andrea F., De Rensis F., Falcini P. Carbohydrate Res. 1997, 298, 75-84; Ott A.J., Brackhagen M., Davtyan A., Nolting B., Boye H., Schoknecht A. and Vogel Ch. J. Carbohydrate Chemistry, 2001, 20, 611-636; Abbas S.A., Barlow J.J. and Matta K.L. Carbohydrate Res. 1981, 88, 51-60.
[2] Kasprzycka A., Ślusarczyk A. and Szeja W. Polish J. Chem. 2001, 75, 1303-1308; Kasprzycka A. and Szeja W. Polish J. Chem. 2005, 79, 329-333.

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