B1 Non-refereed article in a scientific journal
Hydrolysis and intramolecular transesterification of 3 '-thioinosine 3 '-S-phosphorothiolate triester
Authors: Elzagheid MI, Maki E, Kaukinen U, Oivanen M, Lonnberg H
Publication year: 1999
Journal:: Collection Symposium Series
Journal name in source: CHEMISTRY OF NUCLEIC ACID COMPONENTS
Journal acronym: COLL SYMPOS SERIES
Volume: 2
First page : 1
Last page: 5
Number of pages: 5
ISBN: 80-86241-04-1
Abstract
The hydrolytic reactions of the dimethyl ester of 3'-deoxy-3'-thioinosine-3'-S-phosphorothiolate (1b) have been followed by HPLC. At pH > 3, only hydroxide-ion-catalyzed isomerization to the 2'-O-dimethyl phosphate takes place, whereas under more acidic conditions even hydrolysis to the 2'-O- and 3'-S-monomethyl phosphates was observed. Both reactions are acid-catalyzed at pH < 1. The mechanisms of the reactions are discussed in comparison with those of a corresponding RNA dimer analog (IspU, 2) and 3'-O-phosphate alkyl esters.
The hydrolytic reactions of the dimethyl ester of 3'-deoxy-3'-thioinosine-3'-S-phosphorothiolate (1b) have been followed by HPLC. At pH > 3, only hydroxide-ion-catalyzed isomerization to the 2'-O-dimethyl phosphate takes place, whereas under more acidic conditions even hydrolysis to the 2'-O- and 3'-S-monomethyl phosphates was observed. Both reactions are acid-catalyzed at pH < 1. The mechanisms of the reactions are discussed in comparison with those of a corresponding RNA dimer analog (IspU, 2) and 3'-O-phosphate alkyl esters.
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