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The influence of substituents and the environment on the NMR shielding constants of supramolecular complexes based on A-T and A-U base pairs

In the present study, we have theoretically analyzed supramolecular complexes based on the Watson-Crick A-T and A-U base pairs using dispersion-corrected density functional theory (DFT). Hydrogen atoms H8 and/or H6 in the natural adenine and thymine/uracil bases were replaced, respectively, by substituents X8, Y6 = NH - , NH 2 , NH 3 + (N series), O - , OH, OH 2 + (O series), F, Cl or Br (halogen series). We examined the effect of the substituents on the hydrogen-bond lengths, strength and bonding mechanism, and the NMR shielding constants of the C2-adenine and C2-thymine/uracil atoms in the base pairs. The general belief in the literature that there is a direct connection between changes in the hydrogen-bond strength and the C2-adenine shielding constant is conclusively rejected by our computations

The following organizations are thanked for financial support: the Ministerio de Ciencia e Innovación (MICINN, PhD-scholarship BES-2012-052792), the Ministerio de Economía y Competitividad (MINECO, CTQ2014-59212-P and CTQ2015-70851-ERC), GenCat (2014SGR1202 and XRQTC network) and European Fund for Regional Development (FEDER, UNGI10-4E-801)

Royal Society of Chemistry (RSC)

Director: Ministerio de Economía y Competitividad (Espanya)
Autor: Castro Aguilera, Abril Carolina
Swart, Marcel
Guerra, Célia Fonseca
Data: 1 gener 2017
Resum: In the present study, we have theoretically analyzed supramolecular complexes based on the Watson-Crick A-T and A-U base pairs using dispersion-corrected density functional theory (DFT). Hydrogen atoms H8 and/or H6 in the natural adenine and thymine/uracil bases were replaced, respectively, by substituents X8, Y6 = NH - , NH 2 , NH 3 + (N series), O - , OH, OH 2 + (O series), F, Cl or Br (halogen series). We examined the effect of the substituents on the hydrogen-bond lengths, strength and bonding mechanism, and the NMR shielding constants of the C2-adenine and C2-thymine/uracil atoms in the base pairs. The general belief in the literature that there is a direct connection between changes in the hydrogen-bond strength and the C2-adenine shielding constant is conclusively rejected by our computations
The following organizations are thanked for financial support: the Ministerio de Ciencia e Innovación (MICINN, PhD-scholarship BES-2012-052792), the Ministerio de Economía y Competitividad (MINECO, CTQ2014-59212-P and CTQ2015-70851-ERC), GenCat (2014SGR1202 and XRQTC network) and European Fund for Regional Development (FEDER, UNGI10-4E-801)
Format: application/pdf
Accés al document: http://hdl.handle.net/10256/14478
Llenguatge: eng
Editor: Royal Society of Chemistry (RSC)
Col·lecció: info:eu-repo/semantics/altIdentifier/doi/10.1039/C7CP00397H
info:eu-repo/semantics/altIdentifier/issn/1463-9076
info:eu-repo/semantics/altIdentifier/eissn/1463-9084
info:eu-repo/grantAgreement/MINECO//CTQ2014-59212-P/ES/SPIN STATE AND ENZYMATIC CATALYSIS BASED ON BOTTOM-UP COMPUTATIONAL DESIGN/
info:eu-repo/grantAgreement/MINECO//CTQ2015-70851-ERC/ES/SPIN STATE CATALYSIS THROUGH DENSITY-CONSISTENT MOLECULAR MODELLING/
Drets: Tots els drets reservats
Matèria: Enllaços químics
Chemical bonds
Funcional de densitat, Teoria del
Density functionals
Títol: The influence of substituents and the environment on the NMR shielding constants of supramolecular complexes based on A-T and A-U base pairs
Tipus: info:eu-repo/semantics/article
Repositori: DUGiDocs

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