C2′-F Stereoconfiguration As a Puckering Switch for Base Stacking at the Dinucleotide Level | Zendy

Céline Moriou | Zendy; Vânia Lúcia da Silva | Zendy; Marcos Joel Vianelli Prado | Zendy; Clément Denhez | Zendy; Oleksandr Plashkevych | Zendy; Jyoti Chattopadhyaya | Zendy; Dominique Guillaume | Zendy; Pascale Clivio | Zendy

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

Author(s) -

Céline Moriou,

Vânia Lúcia da Silva,

Marcos Joel Vianelli Prado,

Clément Denhez,

Oleksandr Plashkevych,

Jyoti Chattopadhyaya,

Dominique Guillaume,

Pascale Clivio

Publication year - 2018

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.7b03186

Subject(s) - stacking , chemistry , intramolecular force , fluorine , base (topology) , stereochemistry , crystallography , organic chemistry , mathematical analysis , mathematics

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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