Preparation, hydrolysis and intramolecular transesterification of 3'-deoxy-3'-thioinosine 3'-S-dimethylphosphorothiolate.
The hydrolytic reactions of the dimethyl ester of 3'-deoxy-3'-thioinosine 3'-S-phosphorothiolate have been followed over a wide aciditiy 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.
Elzagheid
M I
MI
Department of Chemistry, University of Turku, Finland.
Mäki
E
E
Kaukinen
U
U
Oivanen
M
M
Lönnberg
H
H
D002851:Chromatography, High Pressure Liquid; D004951:Esterification; D006868:Hydrolysis; D007700:Kinetics; D013058:Mass Spectrometry; D008956:Models, Chemical; D009705:Nucleosides / Q000138:chemical synthesis*; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D013868:Thioinosine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry
C417422:3'-deoxy-3'-thioinosine-3'-dimethylphosphorothiolate; D009705:Nucleosides; D009711:Nucleotides; D013868:Thioinosine