Polarization in the structures of uracil and thiouracils: Implication for binding with orotidine 5′-monophosphate decarboxylase

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

卷:21

Article

Huang, Sha²  Gronert, Scott¹  Wu, Weiming² 

[1] Virginia Commonwealth Univ, Dept Chem, Richmond, VA 23284 USA

[2] San Francisco State Univ, Dept Chem & Biochem, San Francisco, CA 94132 USA

关键词: Uracil;    Thiouracil;    Dipole moment;    Polarization;    ODCase;    Coupling constant;   

DOI  :  10.1016/j.bmcl.2011.08.109

来源: Elsevier

【 摘 要 】

The structures of the uracil and thiouracils were examined using NMR spectroscopy and crystal structure data when available. The relationships between the extent of polarization and the C5-C6 bond length as well as the H5-H6 coupling constants were probed. It was found that the bond length and coupling constants correlate well with the proton affinities at the carbonyl or thiocarbonyl groups at C4 but not C2. The possible implication in the tighter binding of thiouracil based nucleotides to orotidine-5'-monophosphate decarboxylase was discussed. (C) 2011 Elsevier Ltd. All rights reserved.

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