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- Moriou, Céline, et al.
(författare)
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C2 '-F Stereoconfiguration As a Puckering Switch for Base Stacking at the Dinucleotide Level
- 2018
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Ingår i: Journal of Organic Chemistry. - : AMER CHEMICAL SOC. - 0022-3263 .- 1520-6904. ; 83:4, s. 2473-2478
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Tidskriftsartikel (refereegranskat)abstract
- 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.
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