ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis of saccharide precursors for preparation of potential inhibitors of glycosyltranferases

Ján Hirsch, Miroslav Koóš, and Igor Tvaroška

Center for Glycomics, Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, SK-845 38 Bratislava, Slovakia

E-mail: chemhirs@savba.sk

Received: 4 September 2008  Revised: 22 October 2008  Accepted: 30 October 2008

Abstract: Ethyl 6-O-tert-butyldimethylsilyl-3,4-di-O-acetyl-2-thio-α-D-fructofuranoside (Va), its β-analog (Vb); as well as benzyl 6-O-tert-butyldimethylsilyl-3,4-di-O-acetyl-2-thio-α-D-fructofuranoside (Xa) and its β-analog (Xb), having an unprotected OH group at C-1, were prepared by sequential synthesis starting from commercially available D-fructose. These compounds represent suitable nucleophiles for the preparation of model carbohydrate mimetics of a glycosyltransferase inhibitor type in transition state. The structures of all compounds were confirmed by NMR spectral data and elemental analyses.

Keywords: fructofuranoside - thioglycoside - glycosyltransferases - inhibitors - synthesis

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-009-0008-8

Chemical Papers 63 (3) 329–335 (2009)