The paradoxical thermodynamic basis for the interaction of ethylene glycol, glycine, and sarcosine chains with bovine carbonic anhydrase II: an unexpected manifestation of enthalpy/entropy compensation.

Journal of the American Chemical Society
Vijay M KrishnamurthyGeorge M Whitesides

Abstract

This paper describes a systematic study of the thermodynamics of association of bovine carbonic anhydrase II (BCA) and para-substituted benzenesulfonamides with chains of oligoglycine, oligosarcosine, and oligoethylene glycol of lengths of one to five residues. For all three of these series of ligands, the enthalpy of binding became less favorable, and the entropy less unfavorable, as the chain length of the ligands increased. The dependence on chain length of the enthalpy was almost perfectly compensated by that of the entropy; this compensation resulted in dissociation constants that were independent of chain length for the three series of ligands. Changes in heat capacity were independent of chain length for the three series and revealed that the amount of molecular surface area buried upon protein-ligand complexation did not increase with increasing chain length. Taken together, these data refute a model in which the chains of the ligands interact hydrophobically with the surface of BCA. To explain the data, a model is proposed based on decreasing "tightness" of the protein-ligand interface as the chain length of the ligand increases. This decreasing tightness, as the chain length increases, is reflected in a less favorable...Continue Reading

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Citations

Jul 5, 2006·Quarterly Reviews of Biophysics·George M Whitesides, Vijay M Krishnamurthy
Feb 1, 2007·Journal of the American Chemical Society·Vijay M KrishnamurthyGeorge M Whitesides
Apr 5, 2007·Journal of the American Chemical Society·D K SrivastavaDavid W Christianson
Jun 23, 2011·Journal of the American Chemical Society·Erin M WilfongTerry L Gustafson
Jul 28, 2011·Journal of the American Chemical Society·Jasmin MecinovićGeorge M Whitesides
Oct 20, 2011·Journal of the American Chemical Society·James M MyslinskiStephen F Martin
Nov 18, 2011·Journal of the American Chemical Society·Eric T MackGeorge M Whitesides
Nov 22, 2011·Journal of the American Chemical Society·Nandhini PonnuswamyJeremy K M Sanders
Aug 13, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Andrew LeeGeorge M Whitesides
Nov 15, 2012·Proceedings of the National Academy of Sciences of the United States of America·Andrew T FenleyMichael K Gilson
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Feb 14, 2012·Drug Discovery Today·Patrick Chène
Feb 1, 2008·Journal of Molecular Biology·Adela M CandelFrancisco Conejero-Lara
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Apr 19, 2007·Chemistry, an Asian Journal·Vijay M KrishnamurthyGeorge M Whitesides
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Jan 30, 2015·Angewandte Chemie·Elke PerschFrançois Diederich
Jun 19, 2012·Soft Matter·Christopher ForreyMichael K Gilson

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