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Tautomeric Equilibrium, Stability, and Hydrogen Bonding in 2‘-Deoxyguanosine Monophosphate Complexed with Mg2+
- Source :
- The Journal of Physical Chemistry B. 112:150-157
- Publication Year :
- 2007
- Publisher :
- American Chemical Society (ACS), 2007.
-
Abstract
- The tautomeric equilibrium and hydrogen bonding in nucleotide 2'-deoxyguanosine monophosphate that interacts with hydrated Mg2+ cation (4H2O.Mg[dGMP]) were studied at the MP2/cc-pVDZ//B3LYP/cc-pVDZ and B3LYP/aug-cc-pVTZ//B3LYP/cc-pVDZ levels of theory. The Mg2+ ion forms two inner-shell contacts with the nucleotide, similar to small phosphorylated molecules under physiological conditions. The presence of the phosphate group and the hydrated magnesium cation leads to a change in guanine tautomeric equilibrium of 4H2O.Mg[dGMP] in comparison to free guanine. The influence of the phosphate group and the magnesium cation on tautomeric equilibrium is larger in the anti conformation where the P=O--Mg and Mg--N7 coordinate bonds are formed. The canonical oxo form of guanine is more stable (by 6-8 kcal/mol) than the O6-hydroxo form in anti conformation. Thus, the interaction with Mg2+ ion is capable of further suppressing the likelihood of a spontaneous transient formation of the rare tautomer. In the syn conformation of 4H2O.Mg[dGMP], the interaction of the guanine nucleobase with the phosphate group and the magnesium cation is not as strong as in the anti conformation, and the relative stability of guanine tautomers is close to those in free guanine.
- Subjects :
- Models, Molecular
chemistry.chemical_classification
Molecular Structure
Cations, Divalent
Hydrogen bond
Deoxyguanosine monophosphate
Stereochemistry
Guanine
Deoxyguanine Nucleotides
Hydrogen Bonding
Tautomer
Surfaces, Coatings and Films
Ion
Crystallography
chemistry.chemical_compound
Isomerism
chemistry
Alkane stereochemistry
Materials Chemistry
Molecule
Magnesium
Nucleotide
Physical and Theoretical Chemistry
Subjects
Details
- ISSN :
- 15205207 and 15206106
- Volume :
- 112
- Database :
- OpenAIRE
- Journal :
- The Journal of Physical Chemistry B
- Accession number :
- edsair.doi.dedup.....510b2b1a13d9ef3b54b1a84fdedd01dd