The Energetics of Hydrogen Bonds in Model Systems: Implications for Enzymatic Catalysis
10.1126/science.272.5258.97
Crossref journal-article
American Association for the Advancement of Science (AAAS)
Science (221)
Abstract

Low-barrier or short, strong hydrogen bonds have been proposed to contribute 10 to 20 kilocalories per mole to transition-state stabilization in enzymatic catalysis. The proposal invokes a large increase in hydrogen bond energy when the p K a values of the donor and acceptor (where K a is the acid constant) become matched in the transition state (Δp K a = 0). This hypothesis was tested by investigating the energetics of hydrogen bonds as a function of Δp K a for homologous series of compounds under nonaqueous conditions that are conducive to the formation of low-barrier hydrogen bonds. In all cases, there was a linear correlation between the increase in hydrogen-bond energy and the decrease in Δp K a , as expected from simple electrostatic effects. However, no additional energetic contribution to the hydrogen bond was observed at Δp K a = 0. These results and those of other model studies suggest alternative mechanisms by which hydrogen bonds can contribute to enzymatic catalysis, in accord with conventional electrostatic considerations.

Bibliography

Shan, S., Loh, S., & Herschlag, D. (1996). The Energetics of Hydrogen Bonds in Model Systems: Implications for Enzymatic Catalysis. Science, 272(5258), 97–101.

Authors 3
  1. Shu-ou Shan (first)
  2. Stewart Loh (additional)
  3. Daniel Herschlag (additional)
References 67 Referenced 231
  1. ALBRECHT G, J CHEM SOC F1 80, 553 (1983). / J CHEM SOC F1 by ALBRECHT G (1983)
  2. ALBRECHT G, CARBOXYLIC ACID-N BASE HYDROGEN-BONDS WITH LARGE PROTON POLARIZABILITY IN ACETONITRILE AS A FUNCTION OF THE BASICITY OF THE HYDROGEN-BOND ACCEPTORS, ZEITSCHRIFT FUR NATURFORSCHUNG SECTION A-A JOURNAL OF PHYSICAL SCIENCES 39, 986 (1984). (10.1515/zna-1984-1013) / ZEITSCHRIFT FUR NATURFORSCHUNG SECTION A-A JOURNAL OF PHYSICAL SCIENCES / CARBOXYLIC ACID-N BASE HYDROGEN-BONDS WITH LARGE PROTON POLARIZABILITY IN ACETONITRILE AS A FUNCTION OF THE BASICITY OF THE HYDROGEN-BOND ACCEPTORS by ALBRECHT G (1984)
  3. ALLERHAND A, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 85, 371 (1963). (10.1021/ja00887a001) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY by ALLERHAND A (1963)
  4. ALTMAN L.J., PROTON, DEUTERIUM, AND TRITIUM NUCLEAR MAGNETIC-RESONANCE OF INTRA-MOLECULAR HYDROGEN-BONDS - ISOTOPE EFFECTS AND SHAPE OF POTENTIAL-ENERGY FUNCTION, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 100, 8264 (1978). (10.1021/ja00494a040) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / PROTON, DEUTERIUM, AND TRITIUM NUCLEAR MAGNETIC-RESONANCE OF INTRA-MOLECULAR HYDROGEN-BONDS - ISOTOPE EFFECTS AND SHAPE OF POTENTIAL-ENERGY FUNCTION by ALTMAN L.J. (1978)
  5. BARTL H, NEUTRON-DIFFRACTION STUDY OF VERY SHORT HYDROGEN-BONDS IN COPPER DIHYDROGEN DIPHTHALATE DIHYDRATE, ZEITSCHRIFT FUR KRISTALLOGRAPHIE 152, 161 (1980). / ZEITSCHRIFT FUR KRISTALLOGRAPHIE / NEUTRON-DIFFRACTION STUDY OF VERY SHORT HYDROGEN-BONDS IN COPPER DIHYDROGEN DIPHTHALATE DIHYDRATE by BARTL H (1980)
  6. BEESON C, THERMODYNAMIC DESCRIPTION OF A CONTACT AND SOLVENT-SEPARATED ION-PAIR AS A FUNCTION OF SOLVATION - A MODEL FOR SALT BRIDGES AND PROTON-TRANSFER REACTIONS IN BIOLOGY, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 115, 10275 (1993). (10.1021/ja00075a049) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / THERMODYNAMIC DESCRIPTION OF A CONTACT AND SOLVENT-SEPARATED ION-PAIR AS A FUNCTION OF SOLVATION - A MODEL FOR SALT BRIDGES AND PROTON-TRANSFER REACTIONS IN BIOLOGY by BEESON C (1993)
  7. BIAGINICINGI M, CRYSTAL AND MOLECULAR-STRUCTURE OF TRIS(THIOUREA)COPPER(I) HYDROGEN-O-PHTHALATE - MONOMERIC TRIGONAL PLANAR COPPER(I) COMPLEX, ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE 33, 3772 (1977). (10.1107/S0567740877012059) / ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE / CRYSTAL AND MOLECULAR-STRUCTURE OF TRIS(THIOUREA)COPPER(I) HYDROGEN-O-PHTHALATE - MONOMERIC TRIGONAL PLANAR COPPER(I) COMPLEX by BIAGINICINGI M (1977)
  8. BORDWELL F.G., EQUILIBRIUM ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION, ACCOUNTS OF CHEMICAL RESEARCH 21, 456 (1988). (10.1021/ar00156a004) / ACCOUNTS OF CHEMICAL RESEARCH / EQUILIBRIUM ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION by BORDWELL F.G. (1988)
  9. BORDWELL F.G., EQUILIBRIA INVOLVING ORGANIC-ANIONS IN DIMETHYLSULFOXIDE AND N-METHYLPYRROLIDIN-2-ONE - ACIDITIES, ION-PAIRING, AND HYDROGEN-BONDING, JOURNAL OF ORGANIC CHEMISTRY 45, 3305 (1980). (10.1021/jo01304a034) / JOURNAL OF ORGANIC CHEMISTRY / EQUILIBRIA INVOLVING ORGANIC-ANIONS IN DIMETHYLSULFOXIDE AND N-METHYLPYRROLIDIN-2-ONE - ACIDITIES, ION-PAIRING, AND HYDROGEN-BONDING by BORDWELL F.G. (1980)
  10. BORDWELL F.G., ACIDITIES AND HYDROGEN-BONDING OF PHENOLS IN DIMETHYLSULFOXIDE, JOURNAL OF ORGANIC CHEMISTRY 49, 1424 (1984). (10.1021/jo00182a020) / JOURNAL OF ORGANIC CHEMISTRY / ACIDITIES AND HYDROGEN-BONDING OF PHENOLS IN DIMETHYLSULFOXIDE by BORDWELL F.G. (1984)
  11. BORS D.A., CARBON ACIDITY .67. THE INDICATOR SCALE OF CESIUM ION-PAIRS IN TETRAHYDROFURAN, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 107, 6975 (1985). (10.1021/ja00310a038) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / CARBON ACIDITY .67. THE INDICATOR SCALE OF CESIUM ION-PAIRS IN TETRAHYDROFURAN by BORS D.A. (1985)
  12. CALDWELL G, ANION ALCOHOL HYDROGEN-BOND STRENGTHS IN THE GAS-PHASE, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 106, 4660 (1984). (10.1021/ja00329a002) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / ANION ALCOHOL HYDROGEN-BOND STRENGTHS IN THE GAS-PHASE by CALDWELL G (1984)
  13. CLELAND W.W., LOW-BARRIER HYDROGEN-BONDS AND LOW FRACTIONATION FACTOR BASES IN ENZYMATIC-REACTIONS, BIOCHEMISTRY 31, 317 (1992). (10.1021/bi00117a001) / BIOCHEMISTRY / LOW-BARRIER HYDROGEN-BONDS AND LOW FRACTIONATION FACTOR BASES IN ENZYMATIC-REACTIONS by CLELAND W.W. (1992)
  14. CLELAND W.W., LOW-BARRIER HYDROGEN-BONDS AND ENZYMATIC CATALYSIS, SCIENCE 264, 1887 (1994). (10.1126/science.8009219) / SCIENCE / LOW-BARRIER HYDROGEN-BONDS AND ENZYMATIC CATALYSIS by CLELAND W.W. (1994)
  15. DAOPIN S, STRUCTURAL AND THERMODYNAMIC CONSEQUENCES OF BURYING A CHARGED RESIDUE WITHIN THE HYDROPHOBIC CORE OF T4 LYSOZYME, BIOCHEMISTRY 30, 11521 (1991). (10.1021/bi00113a006) / BIOCHEMISTRY / STRUCTURAL AND THERMODYNAMIC CONSEQUENCES OF BURYING A CHARGED RESIDUE WITHIN THE HYDROPHOBIC CORE OF T4 LYSOZYME by DAOPIN S (1991)
  16. DIXON H.P., HYDROGEN-BOND STRENGTH AND CHARGE-DISTRIBUTION IN BIFLUORIDE ION, HF2-. LATTICE ENERGIES OF LIHF2, NAHF2, KHF2, RBHF2, AND CSHF2, JOURNAL OF CHEMICAL PHYSICS 57, 4388 (1972). (10.1063/1.1678079) / JOURNAL OF CHEMICAL PHYSICS / HYDROGEN-BOND STRENGTH AND CHARGE-DISTRIBUTION IN BIFLUORIDE ION, HF2-. LATTICE ENERGIES OF LIHF2, NAHF2, KHF2, RBHF2, AND CSHF2 by DIXON H.P. (1972)
  17. EXNER O, CORRELATION ANAL CHE: 439 (1988). / CORRELATION ANAL CHE by EXNER O (1988)
  18. FREY P.A., A LOW-BARRIER HYDROGEN-BOND IN THE CATALYTIC TRIAD OF SERINE PROTEASES, SCIENCE 264, 1927 (1994). (10.1126/science.7661899) / SCIENCE / A LOW-BARRIER HYDROGEN-BOND IN THE CATALYTIC TRIAD OF SERINE PROTEASES by FREY P.A. (1994)
  19. FUNDERBURK L.H., STRUCTURE-REACTIVITY COEFFICIENTS FOR GENERAL ACID CATALYSIS OF SEMI-CARBAZONE FORMATION, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 100, 6708 (1978). (10.1021/ja00489a026) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / STRUCTURE-REACTIVITY COEFFICIENTS FOR GENERAL ACID CATALYSIS OF SEMI-CARBAZONE FORMATION by FUNDERBURK L.H. (1978)
  20. GERLT J.A., UNDERSTANDING THE RATES OF CERTAIN ENZYME-CATALYZED REACTIONS - PROTON ABSTRACTION FROM CARBON ACIDS, ACYL-TRANSFER REACTIONS, AND DISPLACEMENT-REACTIONS OF PHOSPHODIESTERS, BIOCHEMISTRY 32, 11943 (1993). (10.1021/bi00096a001) / BIOCHEMISTRY / UNDERSTANDING THE RATES OF CERTAIN ENZYME-CATALYZED REACTIONS - PROTON ABSTRACTION FROM CARBON ACIDS, ACYL-TRANSFER REACTIONS, AND DISPLACEMENT-REACTIONS OF PHOSPHODIESTERS by GERLT J.A. (1993)
  21. GERLT J.A., AN EXPLANATION FOR RAPID ENZYME-CATALYZED PROTON ABSTRACTION FROM CARBON ACIDS - IMPORTANCE OF LATE TRANSITION-STATES IN CONCERTED MECHANISMS, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 115, 11552 (1993). (10.1021/ja00077a062) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / AN EXPLANATION FOR RAPID ENZYME-CATALYZED PROTON ABSTRACTION FROM CARBON ACIDS - IMPORTANCE OF LATE TRANSITION-STATES IN CONCERTED MECHANISMS by GERLT J.A. (1993)
  22. GILLI P, COVALENT NATURE OF THE STRONG HOMONUCLEAR HYDROGEN-BOND - STUDY OF THE O-H—O SYSTEM BY CRYSTAL-STRUCTURE CORRELATION METHODS, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 116, 909 (1994). (10.1021/ja00082a011) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / COVALENT NATURE OF THE STRONG HOMONUCLEAR HYDROGEN-BOND - STUDY OF THE O-H—O SYSTEM BY CRYSTAL-STRUCTURE CORRELATION METHODS by GILLI P (1994)
  23. GILSON M.K., DESTABILIZATION OF AN ALPHA-HELIX-BUNDLE PROTEIN BY HELIX DIPOLES, PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA 86, 1524 (1989). (10.1073/pnas.86.5.1524) / PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA / DESTABILIZATION OF AN ALPHA-HELIX-BUNDLE PROTEIN BY HELIX DIPOLES by GILSON M.K. (1989)
  24. GORDON J.E., CORRELATION OF HYDROGEN BRIDGING EQUILIBRIA WITH ACIDITY, JOURNAL OF ORGANIC CHEMISTRY 26, 738 (1961). (10.1021/jo01062a024) / JOURNAL OF ORGANIC CHEMISTRY / CORRELATION OF HYDROGEN BRIDGING EQUILIBRIA WITH ACIDITY by GORDON J.E. (1961)
  25. GUNNARSSON G, PROTON AND DEUTERIUM NMR OF HYDROGEN-BONDS - RELATIONSHIP BETWEEN ISOTOPE-EFFECTS AND HYDROGEN-BOND POTENTIAL, CHEMICAL PHYSICS LETTERS 38, 96 (1976). (10.1016/0009-2614(76)80264-3) / CHEMICAL PHYSICS LETTERS / PROTON AND DEUTERIUM NMR OF HYDROGEN-BONDS - RELATIONSHIP BETWEEN ISOTOPE-EFFECTS AND HYDROGEN-BOND POTENTIAL by GUNNARSSON G (1976)
  26. GUTHRIE J.P., ELECTROSTATIC STABILIZATION CAN EXPLAIN THE UNEXPECTED ACIDITY OF CARBON ACIDS IN ENZYME-CATALYZED REACTIONS, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 115, 11569 (1993). (10.1021/ja00077a063) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / ELECTROSTATIC STABILIZATION CAN EXPLAIN THE UNEXPECTED ACIDITY OF CARBON ACIDS IN ENZYME-CATALYZED REACTIONS by GUTHRIE J.P. (1993)
  27. HERSCHLAG D, THE IMPORTANCE OF BEING RIBOSE AT THE CLEAVAGE SITE IN THE TETRAHYMENA RIBOZYME REACTION, BIOCHEMISTRY 32, 8312 (1993). (10.1021/bi00083a035) / BIOCHEMISTRY / THE IMPORTANCE OF BEING RIBOSE AT THE CLEAVAGE SITE IN THE TETRAHYMENA RIBOZYME REACTION by HERSCHLAG D (1993)
  28. HIBBERT F, ADV PHYS ORG CHEM 26, 255 (1990). / ADV PHYS ORG CHEM by HIBBERT F (1990)
  29. HINE J, STRUCTURAL EFFECTS ON RATES AND EQUILIBRIA .15. HYDROGEN-BONDED INTERMEDIATES AND STEPWISE MECHANISMS FOR PROTON-EXCHANGE REACTIONS BETWEEN OXYGEN-ATOMS IN HYDROXYLIC SOLVENTS, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 94, 5766 (1972). (10.1021/ja00771a038) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / STRUCTURAL EFFECTS ON RATES AND EQUILIBRIA .15. HYDROGEN-BONDED INTERMEDIATES AND STEPWISE MECHANISMS FOR PROTON-EXCHANGE REACTIONS BETWEEN OXYGEN-ATOMS IN HYDROXYLIC SOLVENTS by HINE J (1972)
  30. HINE J, PHYSICAL ORGANIC CHE: CH4 (1962). / PHYSICAL ORGANIC CHE by HINE J (1962)
  31. JENCKS W.P., BINDING-ENERGY, SPECIFICITY, AND ENZYMIC CATALYSIS - CIRCE EFFECT, ADVANCES IN ENZYMOLOGY AND RELATED AREAS OF MOLECULAR BIOLOGY 43, 219 (1975). / ADVANCES IN ENZYMOLOGY AND RELATED AREAS OF MOLECULAR BIOLOGY / BINDING-ENERGY, SPECIFICITY, AND ENZYMIC CATALYSIS - CIRCE EFFECT by JENCKS W.P. (1975)
  32. JENCKS W.P., CATALYSIS CHEM ENZYM: CH6 (1987). / CATALYSIS CHEM ENZYM by JENCKS W.P. (1987)
  33. KASENDE O, INFRARED STUDY OF HYDROGEN-BONDED COMPLEXES INVOLVING PHENOL DERIVATIVES AND POLYFUNCTIONAL BASES .2. 3-METHYL-4-PYRIMIDONE, 1-METHYL-2-PYRIMIDONE, 1,4,4-TRIMETHYLCYTOSINE, AND 1,3-DIMETHYLURACIL, JOURNAL OF PHYSICAL CHEMISTRY 88, 2636 (1984). (10.1021/j150656a042) / JOURNAL OF PHYSICAL CHEMISTRY / INFRARED STUDY OF HYDROGEN-BONDED COMPLEXES INVOLVING PHENOL DERIVATIVES AND POLYFUNCTIONAL BASES .2. 3-METHYL-4-PYRIMIDONE, 1-METHYL-2-PYRIMIDONE, 1,4,4-TRIMETHYLCYTOSINE, AND 1,3-DIMETHYLURACIL by KASENDE O (1984)
  34. KOLTHOFF I.M., SUBSTITUENT EFFECTS ON DISSOCIATION OF BENZOIC ACIDS AND HETEROCONJUGATION OF BENZOATES WITH P-BROMOPHENOL IN ACETONITRILE, N,N-DIMETHYLFORMAMIDE, AND DIMETHYL SULFOXIDE INTRAMOLECULAR HYDROGEN BONDING IN O-HYDROXYBENZOIC ACIDS AND THEIR ANIONS, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 93, 3843 (1971). (10.1021/ja00745a001) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / SUBSTITUENT EFFECTS ON DISSOCIATION OF BENZOIC ACIDS AND HETEROCONJUGATION OF BENZOATES WITH P-BROMOPHENOL IN ACETONITRILE, N,N-DIMETHYLFORMAMIDE, AND DIMETHYL SULFOXIDE INTRAMOLECULAR HYDROGEN BONDING IN O-HYDROXYBENZOIC ACIDS AND THEIR ANIONS by KOLTHOFF I.M. (1971)
  35. KORTUM G, DISSOCIATION CONSTAN (1961). / DISSOCIATION CONSTAN by KORTUM G (1961)
  36. KREEVOY M.M., STRUCTURES AND ISOTOPIC FRACTIONATION FACTORS OF COMPLEXES, A1HA2-1, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 102, 3315 (1980). (10.1021/ja00530a002) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / STRUCTURES AND ISOTOPIC FRACTIONATION FACTORS OF COMPLEXES, A1HA2-1 by KREEVOY M.M. (1980)
  37. KRYGOWSKI T.M., COMPLEMENTARY LEWIS ACID-BASE DESCRIPTION OF SOLVENT EFFECTS .1. ION-ION AND ION-DIPOLE INTERACTIONS, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 97, 2143 (1975). (10.1021/ja00841a026) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / COMPLEMENTARY LEWIS ACID-BASE DESCRIPTION OF SOLVENT EFFECTS .1. ION-ION AND ION-DIPOLE INTERACTIONS by KRYGOWSKI T.M. (1975)
  38. LARSON J.W., STRONG HYDROGEN-BONDING IN GAS-PHASE ANIONS - AN ION-CYCLOTRON RESONANCE DETERMINATION OF FLUORIDE BINDING ENERGETICS TO BRONSTED ACIDS FROM GAS-PHASE FLUORIDE EXCHANGE EQUILIBRIA MEASUREMENTS, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 105, 2944 (1983). (10.1021/ja00348a003) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / STRONG HYDROGEN-BONDING IN GAS-PHASE ANIONS - AN ION-CYCLOTRON RESONANCE DETERMINATION OF FLUORIDE BINDING ENERGETICS TO BRONSTED ACIDS FROM GAS-PHASE FLUORIDE EXCHANGE EQUILIBRIA MEASUREMENTS by LARSON J.W. (1983)
  39. MATTHEWS W.S., EQUILIBRIUM ACIDITIES OF CARBON ACIDS .6. ESTABLISHMENT OF AN ABSOLUTE SCALE OF ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 97, 7006 (1975). (10.1021/ja00857a010) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / EQUILIBRIUM ACIDITIES OF CARBON ACIDS .6. ESTABLISHMENT OF AN ABSOLUTE SCALE OF ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION by MATTHEWS W.S. (1975)
  40. MEOTNER M, THE IONIC HYDROGEN-BOND AND ION SOLVATION .1. NH+=O, NH+=N, AND OH+=O BONDS - CORRELATIONS WITH PROTON AFFINITY - DEVIATIONS DUE TO STRUCTURAL EFFECTS, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 106, 1257 (1984). (10.1021/ja00317a015) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / THE IONIC HYDROGEN-BOND AND ION SOLVATION .1. NH+=O, NH+=N, AND OH+=O BONDS - CORRELATIONS WITH PROTON AFFINITY - DEVIATIONS DUE TO STRUCTURAL EFFECTS by MEOTNER M (1984)
  41. MEOTNER M, THE IONIC HYDROGEN-BOND AND ION SOLVATION .5. OH…O- BONDS - GAS-PHASE SOLVATION AND CLUSTERING OF ALKOXIDE AND CARBOXYLATE ANIONS, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 108, 7525 (1986). (10.1021/ja00284a014) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / THE IONIC HYDROGEN-BOND AND ION SOLVATION .5. OH…O- BONDS - GAS-PHASE SOLVATION AND CLUSTERING OF ALKOXIDE AND CARBOXYLATE ANIONS by MEOTNER M (1986)
  42. MEOTNER M, RELATIVE ACIDITIES OF WATER AND METHANOL AND THE STABILITIES OF THE DIMER ANIONS, JOURNAL OF PHYSICAL CHEMISTRY 90, 6687 (1986). (10.1021/j100283a019) / JOURNAL OF PHYSICAL CHEMISTRY / RELATIVE ACIDITIES OF WATER AND METHANOL AND THE STABILITIES OF THE DIMER ANIONS by MEOTNER M (1986)
  43. MIHALICK J.E. unpublished data.
  44. NADLER E.B., STABLE SIMPLE ENOLS .20. SOLVENT AND ALPHA-SUBSTITUENT AND BETA-SUBSTITUENT EFFECTS ON THE ASSOCIATION WITH HYDROGEN-BOND ACCEPTING SOLVENTS AND THE OH CONFORMATION OF STABLE SIMPLE ENOLS, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 111, 213 (1989). (10.1021/ja00183a033) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / STABLE SIMPLE ENOLS .20. SOLVENT AND ALPHA-SUBSTITUENT AND BETA-SUBSTITUENT EFFECTS ON THE ASSOCIATION WITH HYDROGEN-BOND ACCEPTING SOLVENTS AND THE OH CONFORMATION OF STABLE SIMPLE ENOLS by NADLER E.B. (1989)
  45. PAWLAK Z, PROTON-TRANSFER IN ACETONITRILE - HOMOASSOCIATION AND HETEROASSOCIATION (NHN1)+ N-BASES AND TRIMETHYL-N-OXIDE, ELECTROCHIMICA ACTA 29, 391 (1984). (10.1016/0013-4686(84)87080-2) / ELECTROCHIMICA ACTA / PROTON-TRANSFER IN ACETONITRILE - HOMOASSOCIATION AND HETEROASSOCIATION (NHN1)+ N-BASES AND TRIMETHYL-N-OXIDE by PAWLAK Z (1984)
  46. PERRIN C.L., EVIDENCE FOR A DOUBLE-MINIMUM POTENTIAL FOR INTRAMOLECULAR HYDROGEN-BONDS OF AQUEOUS HYDROGEN MALEATE AND HYDROGEN PHTHALATE ANIONS, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 111, 8010 (1989). (10.1021/ja00202a050) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / EVIDENCE FOR A DOUBLE-MINIMUM POTENTIAL FOR INTRAMOLECULAR HYDROGEN-BONDS OF AQUEOUS HYDROGEN MALEATE AND HYDROGEN PHTHALATE ANIONS by PERRIN C.L. (1989)
  47. PERRIN C.L., SYMMETRIES OF HYDROGEN-BONDS IN MONOANIONS OF DICARBOXYLIC-ACIDS, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 114, 8559 (1992). (10.1021/ja00048a031) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / SYMMETRIES OF HYDROGEN-BONDS IN MONOANIONS OF DICARBOXYLIC-ACIDS by PERRIN C.L. (1992)
  48. PERRIN C.L., SYMMETRIES OF HYDROGEN-BONDS IN SOLUTION, SCIENCE 266, 1665 (1994). (10.1126/science.266.5191.1665) / SCIENCE / SYMMETRIES OF HYDROGEN-BONDS IN SOLUTION by PERRIN C.L. (1994)
  49. RAO S.N., FREE-ENERGY PERTURBATION CALCULATIONS ON BINDING AND CATALYSIS AFTER MUTATING ASN-155 IN SUBTILISIN, NATURE 328, 551 (1987). (10.1038/328551a0) / NATURE / FREE-ENERGY PERTURBATION CALCULATIONS ON BINDING AND CATALYSIS AFTER MUTATING ASN-155 IN SUBTILISIN by RAO S.N. (1987)
  50. ROTHENBERG M.E., EQUILIBRIUM-CONSTANTS FOR THE INTERCONVERSION OF SUBSTITUTED 1-PHENYLETHYL ALCOHOLS AND ETHERS - A MEASUREMENT OF INTRAMOLECULAR ELECTROSTATIC INTERACTIONS, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 107, 1340 (1985). (10.1021/ja00291a038) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / EQUILIBRIUM-CONSTANTS FOR THE INTERCONVERSION OF SUBSTITUTED 1-PHENYLETHYL ALCOHOLS AND ETHERS - A MEASUREMENT OF INTRAMOLECULAR ELECTROSTATIC INTERACTIONS by ROTHENBERG M.E. (1985)
  51. RUBIN J, HYDROGEN BONDING .2. PHENOL INTERACTIONS WITH SUBSTITUTED PYRIDINES, JOURNAL OF PHYSICAL CHEMISTRY 69, 3089 (1965). (10.1021/j100893a045) / JOURNAL OF PHYSICAL CHEMISTRY / HYDROGEN BONDING .2. PHENOL INTERACTIONS WITH SUBSTITUTED PYRIDINES by RUBIN J (1965)
  52. SAUNDERS M, A NEW NMR METHOD FOR MEASURING THE DIFFERENCE BETWEEN CORRESPONDING PROTON AND DEUTERIUM CHEMICAL-SHIFTS - ISOTOPE EFFECTS ON EXCHANGE EQUILIBRIA, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 106, 3098 (1984). (10.1021/ja00323a005) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / A NEW NMR METHOD FOR MEASURING THE DIFFERENCE BETWEEN CORRESPONDING PROTON AND DEUTERIUM CHEMICAL-SHIFTS - ISOTOPE EFFECTS ON EXCHANGE EQUILIBRIA by SAUNDERS M (1984)
  53. SCHEINER S, THE NONEXISTENCE OF SPECIALLY STABILIZED HYDROGEN-BONDS IN ENZYMES, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 117, 6970 (1995). (10.1021/ja00131a020) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / THE NONEXISTENCE OF SPECIALLY STABILIZED HYDROGEN-BONDS IN ENZYMES by SCHEINER S (1995)
  54. SCHMIDEDER H, INFLUENCE OF PHENOL ACIDITY AND SOLVENT POLARITY WITH PHENOL RETINAL SCHIFF-BASE HYDROGEN-BONDS - THERMODYNAMIC PARAMETERS OF BOND FORMATION AND PROTON-TRANSFER, JOURNAL OF MOLECULAR STRUCTURE 161, 87 (1987). (10.1016/0022-2860(87)85064-0) / JOURNAL OF MOLECULAR STRUCTURE / INFLUENCE OF PHENOL ACIDITY AND SOLVENT POLARITY WITH PHENOL RETINAL SCHIFF-BASE HYDROGEN-BONDS - THERMODYNAMIC PARAMETERS OF BOND FORMATION AND PROTON-TRANSFER by SCHMIDEDER H (1987)
  55. SCHWARTZ B, ALPHA-FLUORO ACID AND ALPHA-FLUORO AMIDE ANALOGS OF ACETYL-COA AS INHIBITORS OF CITRATE SYNTHASE - EFFECT OF PK(A) MATCHING ON BINDING-AFFINITY AND HYDROGEN-BOND LENGTH, BIOCHEMISTRY 34, 15459 (1995). (10.1021/bi00047a010) / BIOCHEMISTRY / ALPHA-FLUORO ACID AND ALPHA-FLUORO AMIDE ANALOGS OF ACETYL-COA AS INHIBITORS OF CITRATE SYNTHASE - EFFECT OF PK(A) MATCHING ON BINDING-AFFINITY AND HYDROGEN-BOND LENGTH by SCHWARTZ B (1995)
  56. SCHWARTZ B, A SIMPLE METHOD FOR DETERMINING THE RELATIVE STRENGTHS OF NORMAL AND LOW-BARRIER HYDROGEN-BONDS IN SOLUTION - IMPLICATIONS TO ENZYME CATALYSIS, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 117, 11902 (1995). (10.1021/ja00153a011) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / A SIMPLE METHOD FOR DETERMINING THE RELATIVE STRENGTHS OF NORMAL AND LOW-BARRIER HYDROGEN-BONDS IN SOLUTION - IMPLICATIONS TO ENZYME CATALYSIS by SCHWARTZ B (1995)
  57. SHAN S unpublished data.
  58. SHERRY A.D., LINEAR ENTHALPY-SPECTRAL SHIFT CORRELATIONS FOR 2,2,2-TRIFLUOROETHANOL, JOURNAL OF PHYSICAL CHEMISTRY 74, 3535 (1970). (10.1021/j100713a017) / JOURNAL OF PHYSICAL CHEMISTRY / LINEAR ENTHALPY-SPECTRAL SHIFT CORRELATIONS FOR 2,2,2-TRIFLUOROETHANOL by SHERRY A.D. (1970)
  59. STAHL N, HYDROGEN-BONDING BETWEEN SOLUTES IN AQUEOUS-SOLUTION, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 108, 4196 (1986). (10.1021/ja00274a058) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / HYDROGEN-BONDING BETWEEN SOLUTES IN AQUEOUS-SOLUTION by STAHL N (1986)
  60. TAFT R.W., STUDIES OF HYDROGEN-BONDED COMPLEX FORMATION WITH P-FLUOROPHENOL. V. LINEAR FREE ENERGY RELATIONSHIPS WITH OH REFERENCE ACIDS, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 91, 4801 (1969). (10.1021/ja01045a038) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / STUDIES OF HYDROGEN-BONDED COMPLEX FORMATION WITH P-FLUOROPHENOL. V. LINEAR FREE ENERGY RELATIONSHIPS WITH OH REFERENCE ACIDS by TAFT R.W. (1969)
  61. TONG H.X., 2-AMINO-3-KETOBUTYRATE-COA LIGASE FROM BEEF-LIVER MITOCHONDRIA - AN NMR SPECTROSCOPIC STUDY OF LOW-BARRIER HYDROGEN-BONDS OF A PYRIDOXAL 5′-PHOSPHATE-DEPENDENT ENZYME, BIOCHEMISTRY 34, 3362 (1995). (10.1021/bi00010a027) / BIOCHEMISTRY / 2-AMINO-3-KETOBUTYRATE-COA LIGASE FROM BEEF-LIVER MITOCHONDRIA - AN NMR SPECTROSCOPIC STUDY OF LOW-BARRIER HYDROGEN-BONDS OF A PYRIDOXAL 5′-PHOSPHATE-DEPENDENT ENZYME by TONG H.X. (1995)
  62. USHER K.C., A VERY SHORT HYDROGEN-BOND PROVIDES ONLY MODERATE STABILIZATION OF AN ENZYME-INHIBITOR COMPLEX OF CITRATE SYNTHASE, BIOCHEMISTRY 33, 7753 (1994). (10.1021/bi00191a002) / BIOCHEMISTRY / A VERY SHORT HYDROGEN-BOND PROVIDES ONLY MODERATE STABILIZATION OF AN ENZYME-INHIBITOR COMPLEX OF CITRATE SYNTHASE by USHER K.C. (1994)
  63. WALDBURGER C.D., ARE BURIED SALT BRIDGES IMPORTANT FOR PROTEIN STABILITY AND CONFORMATIONAL SPECIFICITY, NATURE STRUCTURAL BIOLOGY 2, 122 (1995). (10.1038/nsb0295-122) / NATURE STRUCTURAL BIOLOGY / ARE BURIED SALT BRIDGES IMPORTANT FOR PROTEIN STABILITY AND CONFORMATIONAL SPECIFICITY by WALDBURGER C.D. (1995)
  64. WARSHEL A, CALCULATIONS OF ENZYMATIC-REACTIONS - CALCULATIONS OF PKA, PROTON-TRANSFER REACTIONS, AND GENERAL ACID CATALYSIS REACTIONS IN ENZYMES, BIOCHEMISTRY 20, 3167 (1981). (10.1021/bi00514a028) / BIOCHEMISTRY / CALCULATIONS OF ENZYMATIC-REACTIONS - CALCULATIONS OF PKA, PROTON-TRANSFER REACTIONS, AND GENERAL ACID CATALYSIS REACTIONS IN ENZYMES by WARSHEL A (1981)
  65. WARSHEL A, ENERGETICS OF ENZYME CATALYSIS, PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA 75, 5250 (1978). (10.1073/pnas.75.11.5250) / PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA / ENERGETICS OF ENZYME CATALYSIS by WARSHEL A (1978)
  66. WILCOX C.S., EXPERIMENTAL AND THEORETICAL-STUDIES OF SUBSTITUENT EFFECTS IN HYDROGEN-BOND BASED MOLECULAR RECOGNITION OF A ZWITTERION BY SUBSTITUTED ARYLUREAS, TETRAHEDRON 51, 621 (1995). (10.1016/0040-4020(94)00921-G) / TETRAHEDRON / EXPERIMENTAL AND THEORETICAL-STUDIES OF SUBSTITUENT EFFECTS IN HYDROGEN-BOND BASED MOLECULAR RECOGNITION OF A ZWITTERION BY SUBSTITUTED ARYLUREAS by WILCOX C.S. (1995)
  67. YAMDAGNI R, HYDROGEN-BONDING ENERGIES TO NEGATIVE IONS FROM GAS-PHASE MEASUREMENTS OF IONIC EQUILIBRIA, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 93, 7139 (1971). (10.1021/ja00755a003) / JOURNAL OF THE AMERICAN CHEMICAL SOCIETY / HYDROGEN-BONDING ENERGIES TO NEGATIVE IONS FROM GAS-PHASE MEASUREMENTS OF IONIC EQUILIBRIA by YAMDAGNI R (1971)
Dates
Type When
Created 18 years, 9 months ago (Oct. 27, 2006, 2:30 p.m.)
Deposited 1 year, 7 months ago (Jan. 12, 2024, 5:03 p.m.)
Indexed 1 month, 3 weeks ago (July 2, 2025, 1:13 p.m.)
Issued 29 years, 4 months ago (April 5, 1996)
Published 29 years, 4 months ago (April 5, 1996)
Published Print 29 years, 4 months ago (April 5, 1996)
Funders 0

None

@article{Shan_1996, title={The Energetics of Hydrogen Bonds in Model Systems: Implications for Enzymatic Catalysis}, volume={272}, ISSN={1095-9203}, url={http://dx.doi.org/10.1126/science.272.5258.97}, DOI={10.1126/science.272.5258.97}, number={5258}, journal={Science}, publisher={American Association for the Advancement of Science (AAAS)}, author={Shan, Shu-ou and Loh, Stewart and Herschlag, Daniel}, year={1996}, month=apr, pages={97–101} }