Hydrolytic reactions of 3 '-deoxy-3 '-thioinosylyl-(3 '-> 5 ')uridine; an RNA dinucleotide containing a 3 '-S-phosphorothiolate linkage

Authors
Elzagheid, MI Oivanen, M Klika, KD Jones, BCNM Cosstick, R Lonnberg, H
Citation
Mi. Elzagheid et al., Hydrolytic reactions of 3 '-deoxy-3 '-thioinosylyl-(3 '-> 5 ')uridine; an RNA dinucleotide containing a 3 '-S-phosphorothiolate linkage, NUCLEOS NUC, 18(9), 1999, pp. 2093-2108
Citations number
24
Categorie Soggetti
Biochemistry & Biophysics
Journal title
NUCLEOSIDES & NUCLEOTIDES
ISSN journal
07328311 → ACNP
Volume
18
Issue
9
Year of publication
1999
Pages
2093 - 2108
Database
ISI
SICI code
0732-8311(1999)18:9<2093:HRO3''>2.0.ZU;2-G
Abstract
The course of hydrolysis of 3'-deoxy-3'-thioinosylyl-(3'-->5')-uridine (Isp U) has been followed by HPLC over a wide pH-range. Two reactions of:the int ernucleosidic thiophosphate linkage compete: (i) cleavage yielding thioinos ine monophosphates and uridine, and (ii) isomerization to the 2',5'-isomer of IspU. Under very acidic conditions, even acid-catalyzed depurination of the inosine moiety is observed. The stability of the thiophosphate linkage and the mechanisms of its rupture are discussed.