A1 Refereed original research article in a scientific journal
Cleavage of the phosphodiester bond of uridylyl-(3 ',5 ')-8-carboxymethylaminoadenosine by hydronium, hydroxide and zinc(II) ions: A model study aimed at elucidating the potential of a carboxylate function as an intramolecular catalyst
Authors: Mikkola S, Oivanen M, Neuvonen K, Piitari S, Ketomaki K, Lonnberg H
Publisher: MARCEL DEKKER INC
Publication year: 2000
Journal: Nucleosides, Nucleotides and Nucleic Acids
Journal name in source: NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
Journal acronym: NUCLEOS NUCLEOT NUCL
Volume: 19
Issue: 10-12
First page : 1675
Last page: 1692
Number of pages: 18
ISSN: 1525-7770
DOI: https://doi.org/10.1080/15257770008045452
Abstract
Uridylyl-(3',5)-8-carboxymethylaminoadenosine has been synthesised, and its transesterification to uridine 2',3'-cyclic phosphate in the presence and absence of Zn2+ ion has been studied. The results show that a carboxylate function in the vicinity of the phosphodiester bond accelerates the metal ion promoted cleavage but not the metal ion independent reaction. Under acidic conditions, the predominant reaction is the cleavage of the side chain, giving the 8-amino derivative.
Uridylyl-(3',5)-8-carboxymethylaminoadenosine has been synthesised, and its transesterification to uridine 2',3'-cyclic phosphate in the presence and absence of Zn2+ ion has been studied. The results show that a carboxylate function in the vicinity of the phosphodiester bond accelerates the metal ion promoted cleavage but not the metal ion independent reaction. Under acidic conditions, the predominant reaction is the cleavage of the side chain, giving the 8-amino derivative.
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