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Quantitative structure\u2013activity relationships between the free energy, enthalpy, and entropy of binding and p<jats:italic>K<\/jats:italic><jats:sub>a<\/jats:sub> and log\u2009<jats:italic>P<\/jats:italic> of the ligands allowed the evaluation of the thermodynamic parameters in terms of the two independent effects of fluorination on the ligand: its electrostatic potential and its hydrophobicity. The parameters were partitioned to the three different structural interactions between the ligand and BCA: the Zn<jats:sup>II<\/jats:sup> cofactor\u2013sulfonamide bond (\u224865\u2009% of the free energy of binding), the hydrogen bonds between the ligand and BCA (\u224810\u2009%), and the contacts between the phenyl ring of the ligand and BCA (\u224825\u2009%). Calorimetry revealed that all of the ligands studied bind in a 1:1 stoichiometry with BCA; this result was confirmed by <jats:sup>19<\/jats:sup>F\u2005NMR spectroscopy and X\u2010ray crystallography (for complexes with human carbonic anhydrase\u2005II).<\/jats:p>","DOI":"10.1002\/asia.200600360","type":"journal-article","created":{"date-parts":[[2006,12,14]],"date-time":"2006-12-14T04:47:48Z","timestamp":1166071668000},"page":"94-105","source":"Crossref","is-referenced-by-count":57,"title":["Thermodynamic Parameters for the Association of Fluorinated Benzenesulfonamides with Bovine Carbonic Anhydrase\u2005II"],"prefix":"10.1002","volume":"2","author":[{"given":"Vijay\u2005M.","family":"Krishnamurthy","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Brooks\u2005R.","family":"Bohall","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chu\u2010Young","family":"Kim","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Demetri\u2005T.","family":"Moustakas","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"David\u2005W.","family":"Christianson","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"George\u2005M.","family":"Whitesides","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2006,12,27]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"V.\u2005M. 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Pharmacol."},{"key":"e_1_2_6_57_2","first-page":"173","volume-title":"Progress in Drug Research","author":"Gupta S. P.","year":"2003"},{"key":"e_1_2_6_58_2","doi-asserted-by":"publisher","DOI":"10.1201\/9780203475300.ch5"},{"key":"e_1_2_6_59_2","unstructured":"\u00a0"},{"key":"e_1_2_6_60_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp015514e"},{"key":"e_1_2_6_61_2","volume-title":"Molecular Driving Forces: Statistical Thermodynamics in Chemistry and Biology","author":"Dill K. 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Jude A.\u2005L. Banerjee M.\u2005K. Haldar S. Manokaran B. Roy S. Mallik D.\u2005K. Srivastava D.\u2005W. Christianson J. Am. Chem. Soc.2006 128 3011\u20133018). Kim et\u2005al. reported that two molecules of 4\u2010(aminosulfonyl)\u2010N\u2010[(2 3 4 5 6\u2010pentafluorophenyl)methyl]benzamide bind to one molecule of a mutant of HCA\u2005II (Phe\u2010131\u2192Val) in the crystal with one ligand bound to the ZnIIcofactor and the second bound outside the active site.[16]This ligand binds with a 1:1 stoichiometry with the HCA mutant in solution.","DOI":"10.1021\/ja057257n"},{"key":"e_1_2_6_78_2","unstructured":"According to the data of Gerig and co\u2010workers there is no peak apparent at the chemical shift of the free ligand until the ligand\u2010to\u2010protein stoichiometry is greater than 2:1. Assuming that free ligand was present at about 7\u2009% (but below the limit of detection by19F\u2005NMR spectroscopy) and given the total concentration of CA of 1\u2005mM we calculated a value forKdobsfor this presumptive secondary site of about 5\u2005\u03bcM."},{"key":"e_1_2_6_79_2","unstructured":"Computation for sequence alignment was performed at the SIB with the BLAST network service from ExPASy: http:\/\/www.expasy.org\/cgi\u2010bin\/blast.pl."},{"key":"e_1_2_6_80_2","doi-asserted-by":"crossref","first-page":"26P","DOI":"10.1042\/bj1200026P","volume":"120","author":"Kernohan J. C.","year":"1970","journal-title":"Biochem. J."},{"key":"e_1_2_6_81_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(19)74305-1"},{"key":"e_1_2_6_82_2","volume-title":"Catalysis in Chemistry and Enzymology","author":"Jencks W. P.","year":"1987"},{"key":"e_1_2_6_83_2","unstructured":"\u00a0"},{"key":"e_1_2_6_84_2","first-page":"141","volume":"85","author":"Nyman P. 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