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Observation of two N 2 ‐isobutyrylguanine tautomers by NMR spectroscopy
Author(s) -
Yang Lijing,
Li Jia,
Simionescu Razvan,
Yan Hongbin
Publication year - 2013
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.3901
Subject(s) - tautomer , chemistry , nuclear magnetic resonance spectroscopy , spectroscopy , dimethyl sulfoxide , dichloromethane , guanine , enthalpy , sulfoxide , computational chemistry , stereochemistry , organic chemistry , thermodynamics , nucleotide , biochemistry , physics , quantum mechanics , solvent , gene
N 2 ‐Isobutyrylguanine was prepared by treatment of guanine with isobutyryl chloride. Two tautomers, 1,7‐dihydro‐2‐(isobutyroyl)amino‐6 H ‐purin‐6‐one and 1,9‐dihydro‐2‐(isobutyroyl)amino‐6 H ‐purin‐6‐one, were identified in almost 1 : 1 ratio in dichloromethane–dimethyl sulfoxide (1 : 1 v/v) by NMR spectroscopy. By using the selective‐inversion experiments, enthalpy, entropy, and free energy for activation were determined. This work represents the first report of guanine tautomers observed directly by NMR spectroscopy. Copyright © 2012 John Wiley & Sons, Ltd.