A theoretical investigation of sugar and phosphate contributions to the activation barriers of guanine methylation by carcinogenic methane diazonium ion

Arturo Rojas, Samantha Cabal, George Papadantonakis

Research output: Contribution to journalArticle

Abstract

Feedback from electrostatic potential and local ionization potential maps provides evidence that in the gas phase electrostatic interactions cause the activation barriers of guanine methylation by methane diazonium ion at the N7 site to increase upon addition of sugar and phosphate moieties, from 24.6 kcal/mol with the 6–31 + G∗ basis set to 29.87 kcal/mol with the 6–311 + G (2df, 2p) basis set at the DFT/B3LYP-D3 level of theory. Aqueous activation barriers strongly depend on the interaction of guanine with discrete number of water molecules and, in implicit water, they lie between 4.37 for free guanine to 5.39 kcal/mol for syn-dGMP

LanguageEnglish (US)
Pages24-29
Number of pages6
JournalChemical Physics Letters
Volume714
DOIs
StatePublished - Jan 16 2019

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Sugar Phosphates
methylation
Methylation
guanines
Methane
Guanine
sugars
phosphates
methane
Chemical activation
activation
Ions
electrostatics
ions
Ionization potential
Water
Coulomb interactions
Discrete Fourier transforms
ionization potentials
water

ASJC Scopus subject areas

  • Physics and Astronomy(all)
  • Physical and Theoretical Chemistry

Cite this

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abstract = "Feedback from electrostatic potential and local ionization potential maps provides evidence that in the gas phase electrostatic interactions cause the activation barriers of guanine methylation by methane diazonium ion at the N7 site to increase upon addition of sugar and phosphate moieties, from 24.6 kcal/mol with the 6–31 + G∗ basis set to 29.87 kcal/mol with the 6–311 + G (2df, 2p) basis set at the DFT/B3LYP-D3 level of theory. Aqueous activation barriers strongly depend on the interaction of guanine with discrete number of water molecules and, in implicit water, they lie between 4.37 for free guanine to 5.39 kcal/mol for syn-dGMP−",
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AB - Feedback from electrostatic potential and local ionization potential maps provides evidence that in the gas phase electrostatic interactions cause the activation barriers of guanine methylation by methane diazonium ion at the N7 site to increase upon addition of sugar and phosphate moieties, from 24.6 kcal/mol with the 6–31 + G∗ basis set to 29.87 kcal/mol with the 6–311 + G (2df, 2p) basis set at the DFT/B3LYP-D3 level of theory. Aqueous activation barriers strongly depend on the interaction of guanine with discrete number of water molecules and, in implicit water, they lie between 4.37 for free guanine to 5.39 kcal/mol for syn-dGMP−

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