ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7
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
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.
Chemical Papers 63 (3) 329–335 (2009)