Observation of two N2-isobutyrylguanine tautomers by NMR spectroscopy.
Lijing Yang, Jia Li, Razvan Simionescu, Hongbin Yan
Index: Magn. Reson. Chem. 51(1) , 60-4, (2013)
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Abstract
N(2)-isobutyrylguanine was prepared by treatment of guanine with isobutyryl chloride. Two tautomers, 1,7-dihydro-2-(isobutyroyl)amino-6H-purin-6-one and 1,9-dihydro-2-(isobutyroyl)amino-6H-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.
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