In vitro study demonstrates synthesis of 4′-thioribonucleosides and weak phosphorylation by bovine adenosine kinase, indicating altered substrate activity without enzyme inhibition.
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.
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Leydier et al. (1994) studied this question.
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