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



: Elzagheid MI, Maki E, Kaukinen U, Oivanen M, Lonnberg H

Publisher: MARCEL DEKKER INC

: 2000

Nucleosides, Nucleotides and Nucleic Acids

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS

: NUCLEOS NUCLEOT NUCL

: 19

: 4

: 827

: 838

: 12

: 1525-7770

DOI: https://doi.org/10.1080/15257770008035028


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.



Last updated on 2025-13-10 at 14:15