A New Synthesis of Some 4′-Thio-D-ribonucleosides and Preliminary Enzymatic Evaluation

Abstract

A new synthesis of 4′-thioribonucleosides is presented together with the enzymatic evaluation of the adenosine analogues with respect to adenosine kinase. The 4-thio-D-ribofuranosyl carbohydrate precursor 7 was obtained in good yield from D-ribose and further reacted with adenine and cytosine to give the α and β anomers of 4′-thioadenosine and 4′-thiocytidine, respectively. 4′-thio-β-D-adenosine, 12β. is a poor substrate for bovine liver adenosine kinase but does not show substrate inhibition of the enzyme.