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C2 '-F Stereoconfiguration As a Puckering Switch for Base Stacking at the Dinucleotide Level
CNRS, Inst Chim Subst Nat, Gif Sur Yvette, France.
Univ Fed Juiz de Fora, Dept Quim, ICE, BR-Juiz De Fora, MG, Brazil.
Univ Fed Juiz de Fora, Dept Quim, ICE, BR-Juiz De Fora, MG, Brazil.
Univ Reims, Inst Chim Mol Reims, CNRS, UMR 7312,UFR Pharm, 51 Rue Cognacq Jay, Reims, France; Univ Reims, Multiscale Mol Modelling Platform, UFR Sci Exactes & Nat, Reims, France.
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2018 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 83, no 4, p. 2473-2478Article in journal (Refereed) Published
Abstract [en]

Fluorine configuration at C2′ of the bis(2′-fluorothymidine) dinucleotide is demonstrated to drive intramolecular base stacking. 2′-β F-Configuration drastically reduces stacking compared to the 2′-α series. Hence, base stacking emerges as being tunable by the C2′-F stereoconfiguration through dramatic puckering variations scrutinized by NMR and natural bond orbital analysis. Accordingly, 2′-β F-isomer photoreactivity is significantly reduced compared to that of the 2′-α F-isomer.

Place, publisher, year, edition, pages
AMER CHEMICAL SOC , 2018. Vol. 83, no 4, p. 2473-2478
National Category
Organic Chemistry
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URN: urn:nbn:se:uu:diva-351016DOI: 10.1021/acs.joc.7b03186ISI: 000427094200085PubMedID: 29364674OAI: oai:DiVA.org:uu-351016DiVA, id: diva2:1209892
Funder
Swedish Research CouncilEU, European Research CouncilNational Supercomputer Centre (NSC), SwedenAvailable from: 2018-05-24 Created: 2018-05-24 Last updated: 2018-05-25Bibliographically approved

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Plashkevych, OleksandrChattopadhyaya, Jyoti

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