C2′-F Stereoconfiguration As a Puckering Switch for Base Stacking at the Dinucleotide Level
| Autor: | Dominique Guillaume, Jyoti Chattopadhyaya, Clément Denhez, Marcos Joel Vianelli Prado, Oleksandr Plashkevych, Céline Moriou, Adilson David da Silva, Pascale Clivio |
|---|---|
| Přispěvatelé: | Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Universidade Federal de Juiz de Fora (UFJF), Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Uppsala University |
| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
0301 basic medicine
Chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry Stacking chemistry.chemical_element 010402 general chemistry 01 natural sciences 0104 chemical sciences 03 medical and health sciences Crystallography 030104 developmental biology Intramolecular force Fluorine [CHIM.OTHE]Chemical Sciences/Other Natural bond orbital |
| Zdroj: | Journal of Organic Chemistry Journal of Organic Chemistry, American Chemical Society, 2018, 83 (4), pp.2473-2478. ⟨10.1021/acs.joc.7b03186⟩ |
| ISSN: | 0022-3263 1520-6904 |
| DOI: | 10.1021/acs.joc.7b03186⟩ |
| Popis: | International audience; 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. |
| Databáze: | OpenAIRE |
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