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



: Elzagheid MI, Oivanen M, Klika KD, Jones BCNM, Cosstick R, Lonnberg H

Publisher: MARCEL DEKKER INC

: 1999

: Nucleosides & nucleotides

: NUCLEOSIDES & NUCLEOTIDES

: NUCLEOS NUCLEOT

: 18

: 9

: 2093

: 2108

: 16

: 0732-8311

DOI: https://doi.org/10.1080/07328319908044866


The course of hydrolysis of 3'-deoxy-3'-thioinosylyl-(3'-->5')-uridine (IspU) has been followed by HPLC over a wide pH-range. Two reactions of:the internucleosidic thiophosphate linkage compete: (i) cleavage yielding thioinosine 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.



Last updated on 2025-13-10 at 13:44