The mechanism of the metal ion promoted cleavage of RNA phosphodiester bonds involves a general acid catalysis by the metal aquo ion on the departure of the leaving group



: Mikkola S, Stenman E, Nurmi K, Yousefi-Salakdeh E, Stromberg R, Lonnberg H

Publisher: ROYAL SOC CHEMISTRY

: 1999

: Royal Society of Chemistry. Journal: Perkin Transactions 2

: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2

: J CHEM SOC PERK T 2

: 8

: 1619

: 1625

: 7

: 0300-9580

DOI: https://doi.org/10.1039/a903691a


A series of uridine 3'-alkyl phosphates and 3'-aryl phosphates were synthesised and their cleavage was studied in the presence of Zn2+ aquo ions. A beta(lg) value was determined for the Zn2+ promoted cleavage of both types of compounds. Comparison of the results obtained to those reported previously for the cleavage of the same substrates in the absence of metal ion catalysts suggests that the alkyl leaving group departs as an alcohol in the presence of metal ion catalysts. Furthermore, metal ion catalysts seem to enhance the departure. The aryl leaving group, in contrast, departs as an oxyanion.



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