Strong hydrogen bonding in molecules and enzymatic complexes

Magnetic Resonance in Chemistry

Volumn 39, Issue SPEC. ISS., 2001, Pages

  Frey, Perry A ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

3 ketosteroid isomerase; Chymotrypsin; Deuterium fractionation factor; Enthalpy of activation; Hydrogen cis cyclohexane 1,2 dicarboxylate; Hydrogen maleate; Low barrier hydrogen bonds; NMR

Indexed keywords

ACETONE; CHEMICAL ACTIVATION; COMPLEXATION; CYCLOHEXANE; DEUTERIUM; ENTHALPY; PHYSICOCHEMICAL PROPERTIES;

3-KETOSTEROID ISOMERASE; CHYMOTRYPSIN; DEUTERIUM FRACTIONATION; DEUTERIUM FRACTIONATION FACTOR; DICARBOXYLATES; ENTHALPIES OF ACTIVATION; FRACTIONATION FACTORS; HYDROGEN CIS-CYCLOHEXANE-1,2-DICARBOXYLATE; HYDROGEN MALEATE; KETOSTEROID ISOMERASE; LOW BARRIER HYDROGEN BONDS; MALEATE;

HYDROGEN BONDS;

EID: 0000741348     PISSN: 07491581     EISSN: None     Source Type: Journal    
DOI: 10.1002/mrc.953     Document Type: Review

References (75)

1. Jeffrey GA. An Introduction to Hydrogen Bonding. Oxford University Press: New York, 1997.
2. Hibbert F, Emsley J. Adv. Phys. Org. Chem. 1990; 26: 255.
3. Pauling L. The Nature of the Chemical Bond. Cornell University Press: Ithaca, NY, 1960.
4. Kreevoy MM, Liang TM. J. Am. Chem. Soc. 1980; 102: 3315.
5. Cleland WW. Biochemistry 1992; 31: 317.
6. Cleland WW, Kreevoy M. Science 1994; 264: 1887.
7. Gerlt JA, Gassman PJ. J. Am. Chem. Soc. 1993; 115: 11552.
8. Frey PA, Whitt SA, Tobin JB. Science 1994; 264: 1927.
9. Markley JL. Biochemistry 1978; 17: 4646.
10. Bachovchin WW. Proc. Natl. Acad. Sci. USA 1985; 82: 7948.
11. Gilli P, Bertalasi V, Ferretti V, Gilli G. J. Am. Chem. Soc. 1994; 116: 909.
12. Gilli P, Bertolasi V, Ferretti V, Gilli G. J. Am. Chem. Soc. 2000; 122: 10405.
13. Schiott B, Iversen BB, Madsen GKH, Larsen FK, Bruice TC. Proc. Natl. Acad. Sci. USA 1998; 95: 12799.
14. Overgaard J, Schiøtt B, Larsen FK, Schultz AJ, MacDonald JC, Iversen BB. Angew. Chem., Int. Ed. Engl. 1999; 38: 1239.
15. Steiner Th, Saenger W. Acta Crystallogr. 1994; B50: 348.
16. Jeffrey G A, Saenger W. Hydrogen Bonding in Biological Structures. Springer: Berlin, 1991.
17. Zundel G. Trends Phys. Chem. 1992; 3: 129.
18. Zundel G, Bohner U. J. Phys. Chem. 1986; 90: 964.
19. Wellner N, Zundel G. J. Mol. Struct. 1994; 317: 249.
20. McDermott A, Ridenour CF. In Encyclopedia of NMR. Grant DM, Harris RK (eds). Wiley: Chichester, 1996; 3820.
21. Mildvan AS, Harris TK, Abeygunawardana C. Methods Enzymol. 1999; 308: 219.
22. Markley JL, Westler WM. Biochemistry 1996; 35: 11092.
23. Murthy AJN, Bhat SN, Rao CNR. J. Chem. Soc. A 1970; 1251.
24. McAllister MA. Can. J. Chem. 1997; 75: 1195.
25. Perrin CL. Annu. Rev. Phys. Org. Chem. 1997; 48: 511.
26. Küppers HÅ, Jessen SM. Z. Kristallogr 1993; 203: 167.
27. Cassidy CS, Lin J, Tobin JB, Frey PA. Bioorg. Chem. 1998; 26: 213.
28. McCoy LL. J. Am. Chem. Soc. 1967; 89: 1673.
29. Westheimer FH, Benfey OT. J. Am. Chem. Soc. 1956; 78: 5309.
30. Brown HC, McDaniel DH, Häfliger O. In Determination of Organic Structures by Physical Methods, vol. 1 Braude EA, Nachod F (eds). Academic Press: New York, 1955; 567.
31. Frey PA, Cleland WW. Bioorg. Chem. 1998; 26: 175.
32. Hess RA, Reinhardt LA. J. Am. Chem. Soc. 1999; 121: 9867.
33. Jarrett RM, Saunders M. J. Am. Chem. Soc. 1985; 107: 2648.
34. Lin J, Frey PA. J. Am. Chem. Soc. 2000; 122: 11258.
35. Mallinson RR, Wozniak K, Smith GT, McCormack KL. J. Am. Chem. Soc. 1997; 119: 11502.
36. Cleland WW, Kreevoy MM, Frey PA. Science 1995; 269: 102.
37. Staab HA, Saupe T. Angew. Chem. 1988; 27: 865.
38. Alder RW. Chem. Rev. 1989; 89: 1215.
39. Einspahr H, Robert JB, Marsh RE, Roberts JD. Acta Crystallogr., Sect. B 1973; 29: 1611.
40. James MNG, Matsushima M. Acta Crystallogr., Sect. B 1976; 32: 1708.
41. Guthrie JP. Chem. Biol. 1996; 3: 163.
42. Denisov GS, Golubev NS, Gindin VA, Limbach HH, Ligay SS, Smimov SN. J. Mol. Struct. 1994; 322: 83.
43. Robillard G, Shulman RG. J. Mol. Biol. 1972; 71: 507.
44. Liang TC, Abeles RH. Biochemistry 1987; 26: 7603.
45. Dega-Szafran Z, Dulewicz E. Org. Magn. Reson. 1981; 16: 241.
46. Dega-Szafran Z, Dulewicz E. J. Chem. Soc., Perkin Trans. 2 1983; 345.
47. Dega-Szafran Z, Szafran M. Heterocycles 1994; 37: 627.
48. Barczynski P, Dega-Szafran Z, Szafran M. J. Chem. Soc., Perkin Trans. 2 1985; 765.
49. Tobin JB, Whitt SA, Cassidy CS, Frey PA. Biochemistry 1995; 34: 6919.
50. Cassidy CS, Reinhart LA, Cleland WW, Frey PA. J. Chem. Soc., Perkin Trans. 2: 1999; 635.
51. Golubev NS, Smirnov SN, Gindin VA, Denisov GS, Benedict H, Limbach H-H. J. Am. Chem. Soc. 1994; 116: 12055.
52. Smirnov SN, Golubev NS, Denisov GS, Benedict H, Schah-Mohammedi P, Limbach HH. J. Am. Chem. Soc. 1996; 118: 4094.
53. Larsen TL, Wedekind JE, Rayment I, Reed GH. Biochemistry 1996; 35: 4349.
54. Kuhn P, Knapp M, Soltis SM, Ganshaw G, Thoene M, Bott R. Biochemistry 1998; 37: 13446.
55. Halkides CJ, Wu YQ, Murray CJ. Biochemistry 1996; 35: 15941.
56. Zhong S, Haghjoo K, Kellner C, Jordan F. J. Am. Chem. Soc. 1995; 117: 7048.
57. Brady K, Abeles RA. Biochemistry 1990; 29: 7608.
58. Cassidy CS, Lin J, Frey PA. Biochemistry 1997; 36: 4576.
59. Lin J, Cassidy CS, Frey PA. Biochemistry 1998; 37: 11940.
60. Brady K, Wei A, Ringe D, Abeles RA. Biochemistry 1990; 29: 7600.
61. Neidhart D, Wei Y, Cassidy CS, Lin J, Cleland WW, Frey PA. Biochemistry 2001; 40: 2439.
62. Lin J, Westler WM, Cleland WW, Markley JM, Frey PA. Proc. Natl. Acad. Sci. USA 1998; 95: 14664.
63. Cassidy CS, Lin J, Frey PA. Biochem. Biophys. Res. Commun. 2000; 273: 789.
64. De Santis L, Carloni P. Proteins 1999; 37: 611.
65. Henderson R. Biochem. J. 1971; 124: 13.
66. Craik CS, Roczniak S, Largeman C, Rutter WJ. Science 1987; 237: 909.
67. Warshel A, Papazyan A, Kollman P. Science 1995; 269: 102.
68. Bruice TC, Fife TH, Bruno JJ, Brandon NE. Biochemistry 1962; 1: 7.
69. Zhao Q, Abeygunawardana C, Gittis AG, Mildvan AS. Biochemistry 1997; 36: 14616.
70. Zhao Q, Abeygunawardana C, Talalay P, Mildvan AS. Proc. Natl. Acad. Sci. USA 1996; 93: 8220.
71. Choi C, Ha NC, Kim SW, Kim DH, Park S, Oh BH, Choi KY. Biochemistry 2000; 39: 903.
72. Cho HS, Choi G, Choi KY, Oh BH. Biochemistry 1998; 37: 8325.
73. Gerlt JA, Gassman PG. Biochemistry 1993; 32: 11943.
74. Harris TK, Abeygunawardana C, Mildvan AS. Biochemistry 1997; 36: 14661.
75. Piana S, Carloni P. Proteins 2000; 39: 26-36.