Preparation, hydrolysis and intramolecular transesterification of 3'- deoxy-3'-thioinosine 3'-S-dimethylphosphorothiolate

Article abstract of DOI:10.1080/15257770008035028

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.

Full text of DOI:10.1080/15257770008035028

Nucleosides, Nucleotides and Nucleic Acids
ISSN: 1525-7770 (Print) 1532-2335 (Online) Journal homepage: http://www.tandfonline.com/loi/lncn20
Preparation, Hydrolysis and Intramolecular
Transesterification of 3′-Deoxy-3′-thioinosine 3′-S-
Dimethylphosphorothiolate
Mohamed I. Elzagheid , Esa Mäki , Ulla Kaukinen , Mikko Oivanen & Harri
Lönnberg
To cite this article: Mohamed I. Elzagheid , Esa Mäki , Ulla Kaukinen , Mikko Oivanen & Harri
Lönnberg (2000) Preparation, Hydrolysis and Intramolecular Transesterification of 3′-Deoxy-3′-
thioinosine 3′-S-Dimethylphosphorothiolate, Nucleosides, Nucleotides and Nucleic Acids, 19:4,
827-838, DOI: 10.1080/15257770008035028
To link to this article: http://dx.doi.org/10.1080/15257770008035028
Published online: 24 Sep 2006.
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Date: 05 November 2015, At: 19:26