C2′‑F Stereoconfiguration As a Puckering Switch for Base Stacking at the Dinucleotide Level

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 dram...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-02, Vol.83 (4), p.2473-2478
Main Authors: Moriou, Céline, Da Silva, Adilson D, Vianelli Prado, Marcos Joel, Denhez, Clément, Plashkevych, Oleksandr, Chattopadhyaya, Jyoti, Guillaume, Dominique, Clivio, Pascale
Format: Article
Language:English
Subjects:
Chemical Sciences
Organic chemistry
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Summary: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.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.7b03186