Lability of glycosidic linkages of 2'-thio-ribonucleosides

Article abstract of DOI:10.1016/0040-4020(95)98706-N

2'-Thiouridine 2, 2'-thioadenosine 5 and 2'-thiocytidine 8 undergo glycosidic cleavage in aqueous solution at 25°C at and above pH 6.5. The glycosidic linkages of [1-β-D-(2-thioarabinofuranosyl)]-adenine 7 and the dimeric disulfides 12a, 12b and 12c, derived from the 2'-thio-ribonucleosides 2, 5 and 8, respectively, are stable under the same neutral and mildly basic conditions. 2'-Thioadenosine 5 and particularly [1-β-D-(2-thioarabinofuranosyl)]adenine 7 are more stable than 2'-deoxyadenosine to acid-catalyzed hydrolysis.