Incorporation of a S-glycosidic linkage into a glyconucleoside changes the conformational preference of both furanose sugars.
A glyconucleoside containing a thioglycoside linkage, namely 1-(3-S-beta-D-ribofuranosyl-2,3-dideoxy-3-thio-beta-D-ribofuranosyl)-thymine, 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.
Buckingham
Joanne
J
Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, UK.
Brazier
John A
JA
Fisher
Julie
J
Cosstick
Richard
R
D002236:Carbohydrate Conformation; D003837:Deoxy Sugars / Q000737:chemistry*; D004187:Disaccharides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D012266:Ribose / Q000737:chemistry*; D013865:Thioglycosides / Q000737:chemistry*
D003837:Deoxy Sugars; D004187:Disaccharides; D013865:Thioglycosides; D012266:Ribose