Nucleosides, nucleotides and nucleic acids p. 827 - 838 (2000)
Update date:2022-08-04
Topics:
Elzagheid, Mohamed I.
Maeki, Esa
Kaukinen, Ulla
Oivanen, Mikko
Loennberg, Harri
The hydrolytic reactions of the dimethyl ester of 3'-deoxy-3'- thioinosine 3'-S-phosphorothiolate have been followed over a wide acidity range by HPLC. At pH > 3, only hydroxide ion catalyzed isomerization to the 2'-dimethylphosphate takes place, whereas under more acidic conditions hydrolysis to the 2'-monomethylphosphate and 3'-S-monomethylphosphorothiolate competes. The latter is the only product accumulating in very acidic solutions (1 M hydrochloric acid). Mechanisms of the reactions are discussed.
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