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Intra‐ and Intermolecular Interactions Influence the Reactivity of RNA Oligonucleotides
Author(s) -
Linjalahti Heidi,
Mikkola Satu
Publication year - 2007
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200790243
Subject(s) - phosphodiester bond , chemistry , oligonucleotide , moiety , reactivity (psychology) , intramolecular force , nucleic acid , nucleoside , intermolecular force , stereochemistry , rna , phosphoramidate , nucleotide , organic chemistry , biochemistry , molecule , dna , medicine , alternative medicine , pathology , gene
The transesterification of RNA oligonucleotides was studied over a wide pH range. The rate constants obtained indicate that, under neutral conditions, oligonucleotides with an adenosine moiety as the 5′‐linked nucleoside can be up to 1000‐fold more reactive than the reference oligonucleotide, a 13‐mer oligo‐U ( 1 ). Experiments with the modified oligonucleotide with N 6 , N 6 ‐dimethyladenosine ( 9 ) as the 5′‐linked nucleoside moiety suggest that the exocyclic amino group is involved in the reaction, influencing the reactivity of the neighboring phosphodiester bond. In addition to such intramolecular interactions, weak intermolecular interactions most probably contribute to the reactivity.