Synthesis and conformational analysis of fluorinated uridine analogues provide insight into a neighbouring-group participation mechanism
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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.
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
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DescriptionFunding: This work was supported by the EPSRC council (Grant number 1398501) and GlaxoSmithKline.
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