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

被引:0
作者
Elzagheid, MI [1 ]
Mäki, E [1 ]
Kaukinen, U [1 ]
Oivanen, M [1 ]
Lönnberg, H [1 ]
机构
[1] Univ Turku, Dept Chem, FIN-20014 Turku, Finland
来源
CHEMISTRY OF NUCLEIC ACID COMPONENTS | 1999年 / 2卷
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中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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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页数:5
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