On the existence of the H3 tautomer of adenine in aqueous solution. Rationalizations based on hybrid quantum mechanics/molecular mechanics predictions
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On the existence of the H3 tautomer of adenine in aqueous solution. Rationalizations based on hybrid quantum mechanics/molecular mechanics predictions. / Aidas, Kestutis; Mikkelsen, Kurt V; Kongsted, Jacob.
I: Physical Chemistry Chemical Physics, Bind 12, Nr. 3, 21.01.2010, s. 761-8.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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TY - JOUR
T1 - On the existence of the H3 tautomer of adenine in aqueous solution. Rationalizations based on hybrid quantum mechanics/molecular mechanics predictions
AU - Aidas, Kestutis
AU - Mikkelsen, Kurt V
AU - Kongsted, Jacob
PY - 2010/1/21
Y1 - 2010/1/21
N2 - The (15)N NMR spectrum of adenine in aqueous solution has been modeled using high-level combined density functional theory/molecular mechanics techniques coupled to a dynamical averaging scheme. The explicit consideration of the three lowest-energy tautomers of adenine-H9, H7 and H3-allows for a well-founded comparison to experimental data. Based on a very good agreement between the predicted and measured (15)N NMR spectrum of adenine, we have estimated the populations of the H9 and H7 tautomers to be around 83 and 17%, respectively-in good agreement with experimental data-and thus concluded that the H3 tautomer is likely not to be formed in aqueous solution. In addition to the (15)N NMR spectrum we have also predicted the (13)C NMR spectrum and (2)J((15)N-H) indirect spin-spin coupling constants. Finally we have calculated and rationalized the general shape of the low-resolution UV absorption spectrum of adenine in water.
AB - The (15)N NMR spectrum of adenine in aqueous solution has been modeled using high-level combined density functional theory/molecular mechanics techniques coupled to a dynamical averaging scheme. The explicit consideration of the three lowest-energy tautomers of adenine-H9, H7 and H3-allows for a well-founded comparison to experimental data. Based on a very good agreement between the predicted and measured (15)N NMR spectrum of adenine, we have estimated the populations of the H9 and H7 tautomers to be around 83 and 17%, respectively-in good agreement with experimental data-and thus concluded that the H3 tautomer is likely not to be formed in aqueous solution. In addition to the (15)N NMR spectrum we have also predicted the (13)C NMR spectrum and (2)J((15)N-H) indirect spin-spin coupling constants. Finally we have calculated and rationalized the general shape of the low-resolution UV absorption spectrum of adenine in water.
KW - Absorption
KW - Adenine
KW - Electrons
KW - Hydrogen
KW - Isomerism
KW - Magnetic Resonance Spectroscopy
KW - Molecular Dynamics Simulation
KW - Quantum Theory
KW - Solutions
KW - Spectrophotometry, Ultraviolet
KW - Water
U2 - 10.1039/b915604f
DO - 10.1039/b915604f
M3 - Journal article
C2 - 20066363
VL - 12
SP - 761
EP - 768
JO - Physical Chemistry Chemical Physics
JF - Physical Chemistry Chemical Physics
SN - 1463-9076
IS - 3
ER -
ID: 33248144