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 |
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| Authors: | Mikkola Satu Mikhailov Sergey N Efimtseva Ekaterina Neuvonen Kari Oivanen Mikko Beigelman Leonid Lönnberg Harri |
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| Institution: | (1) Department of Chemistry, University of Turku, Finland;(2) Department of Chemistry, University of Turku, FIN-20014 Turku, Finland;(3) Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Russia;(4) USA |
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| Abstract: | Stereoisomeric uridylyl(3',5')uridines D,L-UpU andL,D-UpU were synthesised. Their cleavage was followed in thepresence of acid, base and metal ion catalysts to studywhether the stereochemistry affects the inherent reactivity ofthe internucleosidic phosphodiester bond, and whether the lowmolecular weight catalysts can distinguish between thesubstrates. The rate constants obtained were compared to thoseof D,D-UpU. The comparison shows that the stability of thephosphodiester bond does not depend on the stereochemistry ofthe sugar rings. In contrast slight reactivity differences areobserved in the presence of metal ion catalysts, whichsuggests that selective cleavage of stereoisomeric substrateseven by small molecular weight chemical catalysts may bepossible. |
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| Keywords: | molecular evolution phosphodiester bonds RNA sugar configuration stability |
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