A1 Refereed original research article in a scientific journal
A comparative study on the cleavage of stereoisomeric uridylyl(3 ',5 ')uridines [D,D-, D,L- and L,D-UpU] by acid, base and metal ion catalysts
Authors: Mikkola S, Mikhailov SN, Efimtseva E, Neuvonen K, Oivanen M, Beigelman L, Lonnberg H
Publisher: KLUWER ACADEMIC PUBL
Publication year: 2002
Journal: Origins of Life and Evolution of Biospheres
Journal name in source: ORIGINS OF LIFE AND EVOLUTION OF THE BIOSPHERE
Journal acronym: ORIGINS LIFE EVOL B
Volume: 32
Issue: 4
First page : 303
Last page: 310
Number of pages: 8
ISSN: 0169-6149
DOI: https://doi.org/10.1023/A:1020515212130
Abstract
Stereoisomeric uridylyl(3',5')uridines D,L-UpU and L,D-UpU were synthesised. Their cleavage was followed in the presence of acid, base and metal ion catalysts to study whether the stereochemistry affects the inherent reactivity of the internucleosidic phosphodiester bond, and whether the low molecular weight catalysts can distinguish between the substrates. The rate constants obtained were compared to those of D,D-UpU. The comparison shows that the stability of the phosphodiester bond does not depend on the stereochemistry of the sugar rings. In contrast slight reactivity differences are observed in the presence of metal ion catalysts, which suggests that selective cleavage of stereoisomeric substrates even by small molecular weight chemical catalysts may be possible.
Stereoisomeric uridylyl(3',5')uridines D,L-UpU and L,D-UpU were synthesised. Their cleavage was followed in the presence of acid, base and metal ion catalysts to study whether the stereochemistry affects the inherent reactivity of the internucleosidic phosphodiester bond, and whether the low molecular weight catalysts can distinguish between the substrates. The rate constants obtained were compared to those of D,D-UpU. The comparison shows that the stability of the phosphodiester bond does not depend on the stereochemistry of the sugar rings. In contrast slight reactivity differences are observed in the presence of metal ion catalysts, which suggests that selective cleavage of stereoisomeric substrates even by small molecular weight chemical catalysts may be possible.
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