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Updated: Jul 6, 2025

Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
Published on: April 3, 2014
DFT investigation of the regioselective allylation of pyrimidine 2'-deoxynucleosides
H Gérard1, R Lucas-Roper2, R Zerrouki3
1Sorbonne Université, CNRS, LCT, UMR 7616, 4 Place Jussieu, Paris, 75005, France.
Abstract:
To understand the regioselectivity observed in the allylation of pyrimidine nucleosides and to identify the factors directing the reaction, a theoretical study of the regioselective allylation was carried out. Several key points were considered such as: the structure of the deprotonated nucleobase in the presence of Na+; the effect of the solvent on the dissociation and aggregation reactions of thymidine/Na+ ion pair; and the likely allylation reaction mechanisms involved. The results showed that the regioselectivity observed experimentally can be attributed to a greater stability of a dimeric form coupled to an increase of the reaction barrier in THF due to larger Na+ binding to the nucleobase.
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