Files in this item
Synthesis and conformational analysis of fluorinated uridine analogues provide insight into a neighbouring-group participation mechanism
Item metadata
dc.contributor.author | Michailidou, Freideriki | |
dc.contributor.author | Lebl, Tomas | |
dc.contributor.author | Slawin, Alexandra Martha Zoya | |
dc.contributor.author | Sharma, Sunil Vishnuprasadji | |
dc.contributor.author | Brown, Murray | |
dc.contributor.author | Goss, Rebecca | |
dc.date.accessioned | 2020-12-07T15:58:21Z | |
dc.date.available | 2020-12-07T15:58:21Z | |
dc.date.issued | 2020-11-25 | |
dc.identifier | 271266522 | |
dc.identifier | 4455dacc-2add-474a-9d7b-9d0dbd1d2abb | |
dc.identifier | 000597522500001 | |
dc.identifier | 85097036272 | |
dc.identifier.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 | en |
dc.identifier.issn | 1420-3049 | |
dc.identifier.other | ORCID: /0000-0002-0269-3221/work/84314934 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/84314962 | |
dc.identifier.uri | https://hdl.handle.net/10023/21096 | |
dc.description | Funding: This work was supported by the EPSRC council (Grant number 1398501) and GlaxoSmithKline. | en |
dc.description.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. | |
dc.format.extent | 13 | |
dc.format.extent | 2943048 | |
dc.language.iso | eng | |
dc.relation.ispartof | Molecules | en |
dc.subject | Nucleoside | en |
dc.subject | Fluorine | en |
dc.subject | Fluorination | en |
dc.subject | Neighbouring-group participation | en |
dc.subject | Mechanism | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Synthesis and conformational analysis of fluorinated uridine analogues provide insight into a neighbouring-group participation mechanism | en |
dc.type | Journal article | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.identifier.doi | https://doi.org/10.3390/molecules25235513 | |
dc.description.status | Peer reviewed | en |
dc.identifier.url | https://www.mdpi.com/1420-3049/25/23/5513 | en |
This item appears in the following Collection(s)
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.