A1 Refereed original research article in a scientific journal
Preparation, hydrolysis and intramolecular transesterification of 3 '-deoxy-3 '-thioinosine 3 '-S-dimethylphosphorothiolate
Authors: Elzagheid MI, Maki E, Kaukinen U, Oivanen M, Lonnberg H
Publisher: MARCEL DEKKER INC
Publication year: 2000
Journal:: Nucleosides, Nucleotides and Nucleic Acids
Journal name in source: NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
Journal acronym: NUCLEOS NUCLEOT NUCL
Volume: 19
Issue: 4
First page : 827
Last page: 838
Number of pages: 12
ISSN: 1525-7770
DOI: https://doi.org/10.1080/15257770008035028
Abstract
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.
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.
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