Incorporation of a S-glycosidic linkage into a glyconucleoside changes the conformational preference of both furanose sugars

Buckingham, J., Brazier, J. A., Fisher, J. and Cosstick, R. (2007) Incorporation of a S-glycosidic linkage into a glyconucleoside changes the conformational preference of both furanose sugars. Carbohydrate Research, 342 (1). pp. 16-22. ISSN 0008-6215 doi: 10.1016/j.carres.2006.11.007

Abstract/Summary

A glyconucleoside containing a thioglycoside linkage, namely 1-(3-S-beta-D-ribofuranosyl-2,3-dideoxy-3-thio-beta-D-ribofuranosyl)-thy mine, has been prepared through condensation of a suitably protected derivative of 3'-thiothymidine with an activated ribose sugar. NMR has been used to study the conformation of the S-disaccharide and the unmodified O-disaccharide. A full pseudorotational analysis showed that for the S-disaccharide, the ribose and deoxy ribose sugars have a preference for the south and north pucker, respectively; which is the reverse of what is seen for the O-disaccharide. (c) 2006 Elsevier Ltd. All rights reserved.