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Moriou C, Da Silva AD, Vianelli Prado MJ, et al. C2'-F Stereoconfiguration As a Puckering Switch for Base Stacking at the Dinucleotide Level. J Org Chem. 2018;83(4):2473-2478doi: 10.1021/acs.joc.7b03186.
Moriou, C., Da Silva, A. D., Vianelli Prado, M. J., Denhez, C., Plashkevych, O., Chattopadhyaya, J., Guillaume, D., & Clivio, P. (2018). C2'-F Stereoconfiguration As a Puckering Switch for Base Stacking at the Dinucleotide Level. The Journal of organic chemistry, 83(4), 2473-2478. https://doi.org/10.1021/acs.joc.7b03186
Moriou, Céline, et al. "C2'-F Stereoconfiguration As a Puckering Switch for Base Stacking at the Dinucleotide Level." The Journal of organic chemistry vol. 83,4 (2018): 2473-2478. doi: https://doi.org/10.1021/acs.joc.7b03186
Moriou C, Da Silva AD, Vianelli Prado MJ, Denhez C, Plashkevych O, Chattopadhyaya J, Guillaume D, Clivio P. C2'-F Stereoconfiguration As a Puckering Switch for Base Stacking at the Dinucleotide Level. J Org Chem. 2018 Feb 16;83(4):2473-2478. doi: 10.1021/acs.joc.7b03186. Epub 2018 Feb 01. PMID: 29364674.
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J Org Chem. 2018 Feb 16;83(4):2473-2478. doi: 10.1021/acs.joc.7b03186. Epub 2018 Feb 01.

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

The Journal of organic chemistry

Céline Moriou, Adilson D Da Silva, Marcos Joel Vianelli Prado, Clément Denhez, Oleksandr Plashkevych, Jyoti Chattopadhyaya, Dominique Guillaume, Pascale Clivio

Affiliations

  1. Institut de Chimie des Substances Naturelles, CNRS , Gif-sur-Yvette 91198 Cedex, France.
  2. Departamento de Quimica, ICE, Universidade Federal de Juiz de Fora , 36036-900 Juiz de Fora, Minas Gerais, Brazil.
  3. Université de Reims Champagne Ardenne, Institut de Chimie Moléculaire de Reims , CNRS UMR 7312, UFR de Pharmacie, 51 rue Cognacq-Jay, Reims 51096 Cedex, France.
  4. Université de Reims Champagne Ardenne, Multiscale Molecular Modelling Platform, UFR Sciences Exactes et Naturelles , Reims F-51687 Cedex 2, France.
  5. Institute of Cell & Molecular Biology, Program of Chemical Biology, Box 581, Biomedical Center, University of Uppsala , S-75123 Uppsala, Sweden.

PMID: 29364674 DOI: 10.1021/acs.joc.7b03186

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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