Hydrolysis and intramolecular transesterification of 3 '-thioinosine 3 '-S-phosphorothiolate triester

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

: 1999

Collection Symposium Series

CHEMISTRY OF NUCLEIC ACID COMPONENTS

: COLL SYMPOS SERIES

: 2

: 1

: 5

: 80-86241-04-1

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.

Chemical sciences