Thermodynamic Effect of Commplementary Hydrogen Bond Base Pairing on Aromatic stacking Interaction in the Guanine-X-Trp Complex (X=Adenine, Guanine, Cytosine, Thymine)

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概要

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• Four kinds of X-Trp (X=adenine, guanine, cytosine, thymine) were synthesized as model compounds to investigate the effect of complementary hydrogen bond base pairing on the stacking interaction of Trp with nucleic acid base. Association constants (K_a) of these compounds with two guanine derivatives (9-ethylguanine and 9-ethyl-7-methylguanine) were determined by Eadie-Hofstee plots of ^1H-NMR titration experiments, and the thermodynamic parameters (ΔH, ΔS and ΔG) for the respective complexes were obtained by van't Hoff analyses based on the temperature dependence of the K_a values. The complexes were characterized by enthalpy/entropy compensations, where the interaction of cytosine-Trp with guanine derivatives was largely enthalpy-driven, accompanied by a small entropy component, whereas those of remaining complexes were all associated with a large increase in entropy, accompanied by a small positive enthalpy component. The present insight on the binding of X-Trp with a guanine base provides a thermodynamic basis for the importance of cooperative hydrogen bond pairing and aromatic stacking interactions in the specific recognition of a nucleic acid base pair by protein.

• 社団法人日本薬学会の論文
• 1996-11-15

著者

• DOI Mitsunobu

  Osaka University of Pharmaceutical Sciences

• Doi Mitsunobu

  Department Of Physical Chemistry Osaka University Of Pharmaceutical Sciences

• Doi Mitsunobu

  Department Of Pyysical Chemistry Osaka University Of Pharmaceutical Sciences

• ISHIDA Toshimasa

  Department of Pyysical Chemistry, Osaka University of Pharmaceutical Sciences

• TARUI Mariko

  Osaka University of Pharmaceutical Sciences

• NOMOTO Noriko

  Osaka University of Pharmaceutical Sciences

• TARUI Mariko

  Department of Physical Chemistry, Osaka University of Pharmaceutical Sciences

• NOMOTO Noriko

  Department of Physical Chemistry, Osaka University of Pharmaceutical Sciences

• HASEGAWA Yoko

  Department of Physical Chemistry, Osaka University of Pharmaceutical Sciences

• MINOURA Katsuhiko

  Department of Physical Chemistry, Osaka University of Pharmaceutical Sciences

• Ishida T

  Osaka Univ. Pharmaceutical Sci. Osaka

• Ishida Toshimasa

  Department Of Physical Chemistry Osaka University Of Pharmaceutical Sciences

• Hasegawa Yoko

  Department Of Physical Chemistry Osaka University Of Pharmaceutical Sciences

• Hasegawa Yasuhiro

  Department Of Neurology St Marianna University School Of Medicine

• Hasegawa Yoko

  Department Of Biology Faculty Of Science Chiba University

• Ishida T

  Departments Of Biochemistry Shiga University Of Medical Science

• Ishida Toshimasa

  Osaka Univ. Of Pharmaceutical Sciences

• Minoura K

  Department Of Physical Chemistry Osaka University Of Pharmaceutical Sciences

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