Synthesis and conformational analysis of fluorinated uridine analogues provide insight into a neighbouring-group participation mechanism
Abstract
Fluorinated nucleoside analogues have attracted much attention as anticancer and antiviral agents and as probes for enzymatic function. However, the lack of direct synthetic methods, especially for 2′,3′-dideoxy-2′,3′-difluoro nucleosides, hamper their practical utility. In order to design more efficient synthetic methods, a better understanding of the conformation and mechanism of formation of these molecules is important. Herein, we report the synthesis and conformational analysis of a 2′,3′-dideoxy-2′,3′-difluoro and a 2′-deoxy-2′-fluoro uridine derivative and provide an insight into the reaction mechanism. We suggest that the transformation most likely diverges from the SN1 or SN2 pathway, but instead operates via a neighbouring-group participation mechanism.
Citation
Michailidou , F , Lebl , T , Slawin , A M Z , Sharma , S V , Brown , M & Goss , R 2020 , ' Synthesis and conformational analysis of fluorinated uridine analogues provide insight into a neighbouring-group participation mechanism ' , Molecules , vol. 25 , no. 23 , 5513 . https://doi.org/10.3390/molecules25235513
Publication
Molecules
Status
Peer reviewed
ISSN
1420-3049Type
Journal article
Description
Funding: This work was supported by the EPSRC council (Grant number 1398501) and GlaxoSmithKline.Collections
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