Chemical double-mutant cycles: dissecting non-covalent interactions.

Thermodynamic double-mutant cycles and triple-mutant boxes are widely employed for the experimental quantification of non-covalent interactions and cooperative effects in proteins. This review describes the application of these powerful methodologies to the study of non-covalent interactions in synthetic systems.

[1]  C. Urch,et al.  A supramolecular system for quantifying aromatic stacking interactions. , 2001, Chemistry.

[2]  Y. Aoyama,et al.  Simultaneous hydrogen bonding and metal coordination interactions in the two-point fixation of amino acids with a bifunctional metalloporphyrin receptor , 1990 .

[3]  L. Wyns,et al.  Functional interactions among the His40, Glu58 and His92 catalysts of ribonuclease T1 as studied by double and triple mutants. , 1993, Journal of molecular biology.

[4]  C. Hunter,et al.  Cooperativity in the self-assembly of porphyrin ladders. , 2006, Proceedings of the National Academy of Sciences of the United States of America.

[5]  A. Fersht,et al.  A structural double-mutant cycle: estimating the strength of a buried salt bridge in barnase. , 2002, Acta crystallographica. Section D, Biological crystallography.

[6]  E. Cera.  Site-Specific Thermodynamics: Understanding Cooperativity in Molecular Recognition. , 1998 .

[7]  A. Zhong,et al.  Quantifying β-Sheet Stability by Phage Display , 2002 .

[8]  A. Horovitz,et al.  On the choice of reference mutant states in the application of the double-mutant cycle method. , 1996, Protein engineering.

[9]  S. Jusuf,et al.  The role of configurational entropy in biochemical cooperativity. , 2002, Journal of the American Chemical Society.

[10]  L. Makings,et al.  Charge separation in carotenoporphyrin-quinone triads: synthetic, conformational, and fluorescence lifetime studies , 1987 .

[11]  C. Hunter,et al.  Structure–activity relationship for quantifying aromatic interactions† , 1998 .

[12]  C. Wilcox,et al.  MOLECULAR TORSION BALANCE FOR WEAK MOLECULAR RECOGNITION FORCES. EFFECTS OF TILTED-T EDGE-TO-FACE AROMATIC INTERACTIONS ON CONFORMATIONAL SELECTION AND SOLID-STATE STRUCTURE , 1994 .

[13]  C. Tatko,et al.  Investigation of the nature of the methionine–π interaction in β‐hairpin peptide model systems , 2004 .

[14]  T. Schiestel,et al.  Host-guest supramolecular chemistry. 34. The incremental approach to noncovalent interactions: coulomb and van der Waals effects in organic ion pairs , 1992 .

[15]  S. Griffiths-Jones,et al.  Energetics of Weak Interactions in a β-hairpin Peptide: Electrostatic and Hydrophobic Contributions to Stability from Lysine Salt Bridges , 1999 .

[16]  S. Cockroft,et al.  A 1H NMR study of crystal nucleation in solution , 2004 .

[17]  G Schreiber,et al.  The role of Glu73 of barnase in catalysis and the binding of barstar. , 1997, Journal of molecular biology.

[18]  J. G. Vinter,et al.  The role of the counteranion in the cation-pi interaction. , 2003, Chemical communications.

[19]  C. Tatko,et al.  Selective Aromatic Interactions in β-Hairpin Peptides , 2002 .

[20]  H. Reich,et al.  The strength of parallel-displaced arene-arene interactions in chloroform. , 2005, The Journal of organic chemistry.

[21]  C. Urch,et al.  Experimental Measurement of Noncovalent Interactions Between Halogens and Aromatic Rings , 2004, Chembiochem : a European journal of chemical biology.

[22]  C. Hunter,et al.  Complexation-Induced Changes in 1H NMR Chemical Shift for Supramolecular Structure Determination , 1999 .

[23]  F. Diederich,et al.  A weak attractive interaction between organic fluorine and an amide group. , 2004, Angewandte Chemie.

[24]  Nichola L. Davies,et al.  Cooperative binding interactions of glycopeptide antibiotics. , 2002, Journal of the American Chemical Society.

[25]  J. Barcina,et al.  Influence of highly preorganised 7,7-diphenylnorbornane in the free energy of edge-to-face aromatic interactions. , 2001 .

[26]  Alan R. Fersht,et al.  The use of double mutants to detect structural changes in the active site of the tyrosyl-tRNA synthetase (Bacillus stearothermophilus) , 1984, Cell.

[27]  Julius Rebek,et al.  Water-Soluble Receptors for Cyclic-AMP and Their Use for Evaluating Phosphate-Guanidinium Interactions , 1994 .

[28]  C. Tatko,et al.  The geometry and efficacy of cation–π interactions in a diagonal position of a designed β‐hairpin , 2003 .

[29]  C. Urch,et al.  Electrostatic control of aromatic stacking interactions. , 2005, Journal of the American Chemical Society.

[30]  S. Jusuf,et al.  Configurational entropy and cooperativity between ligand binding and dimerization in glycopeptide antibiotics. , 2003, Journal of the American Chemical Society.

[31]  C. Hunter,et al.  How strong is a π-facial hydrogen bond? , 1996 .

[32]  C. Hunter,et al.  Chemical Double-Mutant Cycles for the Measurement of Weak Intermolecular Interactions: Edge-to-Face Aromatic Interactions† , 1996 .

[33]  J. G. Vinter,et al.  Quantitative determination of intermolecular interactions with fluorinated aromatic rings. , 2001, Chemistry.

[34]  C. Hunter,et al.  Quantifying intermolecular interactions: guidelines for the molecular recognition toolbox. , 2004, Angewandte Chemie.

[35]  J. G. Vinter,et al.  Substituent effects on cation–π interactions: A quantitative study , 2002, Proceedings of the National Academy of Sciences of the United States of America.

[36]  G. Ercolani.  Assessment of cooperativity in self-assembly. , 2003, Journal of the American Chemical Society.

[37]  L. Wyns,et al.  Investigation of the functional interplay between the primary site and the subsite of RNase T1: Kinetic analysis of single and multiple mutants for modified substrates , 1994, Proteins.

[38]  C. Hunter,et al.  Cooperativity, partially bound states, and enthalpy-entropy compensation. , 2003, Chemistry & biology.

[39]  C. Hunter,et al.  Desolvation tips the balance: solvent effects on aromatic interactions. , 2006, Chemical communications.

[40]  C. Hunter,et al.  Self-assembly of zinc aminoporphyrins , 1999 .

[41]  A. Fersht,et al.  Estimating the contribution of engineered surface electrostatic interactions to protein stability by using double-mutant cycles. , 1990, Biochemistry.

[42]  J. G. Vinter,et al.  Noncovalent Assembly of [2]Rotaxane Architectures. , 2001, Angewandte Chemie.

[43]  C. Wilcox,et al.  Measurements of Molecular Electrostatic Field Effects in Edge-to-Face Aromatic Interactions and CH-π Interactions with Implications for Protein Folding and Molecular Recognition , 1998 .

[44]  A. Fersht,et al.  Strategy for analysing the co-operativity of intramolecular interactions in peptides and proteins. , 1990, Journal of molecular biology.

[45]  Y. Aoyama,et al.  Molecular recognition. 16. Molecular recognition of quinones: two-point hydrogen-bonding strategy for the construction of face-to-face porphyrin-quinone architectures , 1991 .

[46]  A. Fersht,et al.  Co-operative interactions during protein folding. , 1992, Journal of molecular biology.

[47]  C. Hunter,et al.  Chemical triple-mutant boxes for quantifying cooperativity in intermolecular interactions. , 2002, Chemistry.

[48]  J. Redzic,et al.  Role of hydrogen bond networks and dynamics in positive and negative cooperative stabilization of a protein. , 2005, Biochemistry.

[49]  C. Hunter,et al.  From structure to chemical shift and vice-versa , 2005 .

[50]  C. Hunter,et al.  Synthesis and recognition properties of aromatic amide oligomers: Molecular zippers , 2000 .

[51]  Gianni Chessari,et al.  An evaluation of force-field treatments of aromatic interactions. , 2002, Chemistry.

[52]  George M. Whitesides,et al.  Design, Synthesis, and Characterization of a High-Affinity Trivalent System Derived from Vancomycin and l-Lys-d-Ala-d-Ala , 2000 .

[53]  M. Searle,et al.  Design of beta-sheet systems for understanding the thermodynamics and kinetics of protein folding. , 2004, Current opinion in structural biology.

[54]  C. Hunter,et al.  Substituent effects on edge-to-face aromatic interactions. , 2002, Chemistry.

[55]  C. Hunter,et al.  Quantitative measurements of edge-to-face aromatic interactions by using chemical double-mutant cycles. , 2001, Chemistry.

[56]  Jeremy G. Vinter,et al.  Extended electron distributions applied to the molecular mechanics of some intermolecular interactions , 1994, J. Comput. Aided Mol. Des..

[57]  H. Reich,et al.  Off-center oxygen-arene interactions in solution: a quantitative study. , 2005, The Journal of organic chemistry.

[58]  Kwang S. Kim,et al.  Aromatic-aromatic ring interaction revisited with model compounds of Wilcox. , 1997, Journal of biomolecular structure & dynamics.

[59]  J. G. Vinter,et al.  Quantification of functional group interactions in transition states. , 2003, Journal of the American Chemical Society.

[60]  Marcey L. Waters,et al.  Comparison of C−H···π and Hydrophobic Interactions in a β-Hairpin Peptide: Impact on Stability and Specificity , 2004 .

[61]  J. Berg,et al.  Electrostatic interactions across a beta-sheet. , 1997, Biochemistry.