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Journal of the American Chemical Society

Volumn 126, Issue 16, 2004, Pages 5164-5173

A Comparison of the Electrophilic Reactivities of Zn2+ and Acetic Acid as Catalysts of Enolization: Imperatives for Enzymatic Catalysis of Proton Transfer at Carbon

(2) Crugeiras, Juan b Richard, John P a

a UNIVERSITY AT BUFFALO (United States)

b UNIVERSITY OF SANTIAGO DE COMPOSTELA (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; CATALYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHASE TRANSITIONS; POSITIVE IONS; SOLVENTS; ZINC COMPOUNDS;

DEPROTONATION; TRANSITION STATES;

REACTION KINETICS;

ACETIC ACID; ACETONE; ANION; BUFFER; CARBON; CARBONYL DERIVATIVE; CATION; DEUTERIUM; DEUTERIUM OXIDE; ENZYME; ION; METAL; SOLVENT; WATER; ZINC CHLORIDE; ZINC ION;

ARTICLE; CATALYSIS; CATALYST; CHELATION; CHEMICAL REACTION; COMPARATIVE STUDY; PHASE TRANSITION; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; TEMPERATURE;

ACETATES; ACETIC ACID; ACETONE; CATALYSIS; CATIONS, DIVALENT; DEUTERIUM; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; PROTONS; ZINC;

EID: 1942489246 PISSN: 00027863 EISSN: None Source Type: Journal
DOI: 10.1021/ja049489c Document Type: Article

Times cited : (14)

References (62)

1
- 85021622696
- Gerlt, J. A.; Kozarich, J. W.; Kenyon, G. L.; Gassman, P. G. J. Am. Chem. Soc. 1991, 113, 9667-9669.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 9667-9669
- Gerlt, J.A.¹ Kozarich, J.W.² Kenyon, G.L.³ Gassman, P.G.⁴

2
- 1842800737
- Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1992, 114, 5928-5934.
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 5928-5934
- Gerlt, J.A.¹ Gassman, P.G.²

3
- 0027133903
- Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552-11568.
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 11552-11568
- Gerlt, J.A.¹ Gassman, P.G.²

4
- 0027420398
- Gerlt, J. A.; Gassman, P. G. Biochemistry 1993, 32, 11943-11952.
- (1993) Biochemistry , vol.32 , pp. 11943-11952
- Gerlt, J.A.¹ Gassman, P.G.²

5
- 0031127432
- Gerlt, J. A.; Kreevoy, M. M.; Cleland, W. W.; Frey, P. A. Chem. Biol. 1997, 4, 259-267.
- (1997) Chem. Biol. , vol.4 , pp. 259-267
- Gerlt, J.A.¹ Kreevoy, M.M.² Cleland, W.W.³ Frey, P.A.⁴

6
- 0027140350
- Guthrie, J. P.; Kluger, R. J. Am. Chem. Soc. 1993, 115, 11569-11572.
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 11569-11572
- Guthrie, J.P.¹ Kluger, R.²

7
- 0032475836
- Cleland, W. W.; Frey, P. A.; Gerlt, J. A. J. Biol. Chem. 1998, 273, 25529-25532.
- (1998) J. Biol. Chem. , vol.273 , pp. 25529-25532
- Cleland, W.W.¹ Frey, P.A.² Gerlt, J.A.³

8
- 0000556636
- Wiberg, K. B.; Castejon, H. J. Org. Chem. 1995, 60, 6327-6334.
- (1995) J. Org. Chem. , vol.60 , pp. 6327-6334
- Wiberg, K.B.¹ Castejon, H.²

9
- 0014409457
- Gracy, R. W.; Noltmann, E. A. J. Biol. Chem. 1968, 243, 4109-4116.
- (1968) J. Biol. Chem. , vol.243 , pp. 4109-4116
- Gracy, R.W.¹ Noltmann, E.A.²

10
- 0025893928
- Komives, E. A.; Chang, L. C.; Lolis, E.; Tilton, R. F.; Petsko, G. A.; Knowles, J. R. Biochemistry 1991, 30, 3011-3019.
- (1991) Biochemistry , vol.30 , pp. 3011-3019
- Komives, E.A.¹ Chang, L.C.² Lolis, E.³ Tilton, R.F.⁴ Petsko, G.A.⁵ Knowles, J.R.⁶

11
- 0035852828
- Jeffrey, C. J.; Hardré, R.; Salmon, L. Biochemistry 2001, 40, 1560-1564.
- (2001) Biochemistry , vol.40 , pp. 1560-1564
- Jeffrey, C.J.¹ Hardré, R.² Salmon, L.³

12
- 0001603677
- Jencks, W. P. J. Am. Chem. Soc. 1972, 94, 4731-4732.
- (1972) J. Am. Chem. Soc. , vol.94 , pp. 4731-4732
- Jencks, W.P.¹

13
- 0035543093
- Wolfenden, R.; Snider, M. J. Acc. Chem. Res. 2001, 34, 938-945.
- (2001) Acc. Chem. Res. , vol.34 , pp. 938-945
- Wolfenden, R.¹ Snider, M.J.²

14
- 0035819633
- Nagorski, R. W.; Richard, J. P. J. Am. Chem. Soc. 2001, 123, 794-802.
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 794-802
- Nagorski, R.W.¹ Richard, J.P.²

15
- 0035606960
- Richard, J. P.; Amyes, T. L. Curr. Opin. Chem. Biol. 2001, 5, 626-633.
- (2001) Curr. Opin. Chem. Biol. , vol.5 , pp. 626-633
- Richard, J.P.¹ Amyes, T.L.²

16
- 33847805492
- Cox, B. G. J. Am. Chem. Soc. 1974, 96, 6823-6827.
- (1974) J. Am. Chem. Soc. , vol.96 , pp. 6823-6827
- Cox, B.G.¹

17
- 0009168745
- Maria, P. D.; Fontana, A.; Siani, G.; Spinelli, D. Eur. J. Org. Chem. 1998, 1867-1872.
- (1998) Eur. J. Org. Chem. , pp. 1867-1872
- Maria, P.D.¹ Fontana, A.² Siani, G.³ Spinelli, D.⁴

18
- 0036572082
- Fontana, A.; Maria, P. D.; Pierini, M.; Siani, G.; Cerritelli, S.; Macaluso, G. J. Phys. Org. Chem. 2002, 15, 247-257.
- (2002) J. Phys. Org. Chem. , vol.15 , pp. 247-257
- Fontana, A.¹ Maria, P.D.² Pierini, M.³ Siani, G.⁴ Cerritelli, S.⁵ Macaluso, G.⁶

19
- 0001469091
- Eustace, S. J.; McCann, G. M.; More O'Ferrall, R. A.; Murphy, M. G.; Murray, B. A.; Walsh, S. M. J. Phys. Org. Chem. 1998, 11, 519-528.
- (1998) J. Phys. Org. Chem. , vol.11 , pp. 519-528
- Eustace, S.J.¹ McCann, G.M.² More O'Ferrall, R.A.³ Murphy, M.G.⁴ Murray, B.A.⁵ Walsh, S.M.⁶

20
- 0014430105
- Gracy, R. W.; Noltmann, E. A. J. Biol. Chem. 1968, 243, 5410-5419.
- (1968) J. Biol. Chem. , vol.243 , pp. 5410-5419
- Gracy, R.W.¹ Noltmann, E.A.²

21
- 0000249662
- Hegarty, A. F.; Jencks, W. P. J. Am. Chem. Soc. 1975, 97, 7188-7199.
- (1975) J. Am. Chem. Soc. , vol.97 , pp. 7188-7199
- Hegarty, A.F.¹ Jencks, W.P.²

22
- 0032542691
- Hegarty, A. F.; Dowling, J. P.; Eustace, S. J.; McGarraghy, M. J. Am. Chem. Soc. 1998, 120, 2290-2296.
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 2290-2296
- Hegarty, A.F.¹ Dowling, J.P.² Eustace, S.J.³ McGarraghy, M.⁴

23
- 0001733352
- Hine, J.; Hampton, K. G.; Menon, B. C. J. Am. Chem. Soc. 1967, 89, 2664-2668.
- (1967) J. Am. Chem. Soc. , vol.89 , pp. 2664-2668
- Hine, J.¹ Hampton, K.G.² Menon, B.C.³

24
- 6444222991
- Glasoe, P. K.; Long, F. A. J. Phys. Chem. 1960, 64, 188-190.
- (1960) J. Phys. Chem. , vol.64 , pp. 188-190
- Glasoe, P.K.¹ Long, F.A.²

25
- 0000047442
- Amyes, T. L.; Richard, J. P. J. Am. Chem. Soc. 1992, 114, 10297-10302.
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 10297-10302
- Amyes, T.L.¹ Richard, J.P.²

26
- 0030567338
- Amyes, T. L.; Richard, J. P. J. Am. Chem. Soc. 1996, 118, 3129-3141.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 3129-3141
- Amyes, T.L.¹ Richard, J.P.²

27
- 0033606245
- Richard, J. P.; Nagorski, R. W. J. Am. Chem. Soc. 1999, 121, 4763-4770.
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 4763-4770
- Richard, J.P.¹ Nagorski, R.W.²

28
- 0034605454
- Rios, A.; Amyes, T. L.; Richard, J. P. J. Am. Chem. Soc. 2000, 122, 9373-9385.
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 9373-9385
- Rios, A.¹ Amyes, T.L.² Richard, J.P.³

29
- 0037125519
- Rios, A.; Richard, J. P.; Amyes, T. L. J. Am. Chem. Soc. 2002, 124, 8251-8259.
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 8251-8259
- Rios, A.¹ Richard, J.P.² Amyes, T.L.³

30
- 0037181385
- Richard, J. P.; Williams, G.; O'Donoghue, A. C.; Amyes, T. L. J. Am. Chem. Soc. 2002, 124, 2957-2968.
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 2957-2968
- Richard, J.P.¹ Williams, G.² O'Donoghue, A.C.³ Amyes, T.L.⁴

31
- 0033518558
- Richard, J. P.; Williams, G.; Gao, J. J. Am. Chem. Soc. 1999, 121, 715-726.
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 715-726
- Richard, J.P.¹ Williams, G.² Gao, J.³

32
- 0001327410
- Halkides, C. J.; Frey, P. A.; Tobin, J. B. J. Am. Chem. Soc. 1993, 115, 3332-3333.
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 3332-3333
- Halkides, C.J.¹ Frey, P.A.² Tobin, J.B.³

33
- 0030458467
- Tobin, J. B.; Frey, P. A. J. Am. Chem. Soc. 1996, 118, 12253-12260.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 12253-12260
- Tobin, J.B.¹ Frey, P.A.²

34
- 0000715625
- a = 15.7 for water.
- (1983) Inorg. Chem. , vol.22 , pp. 2297-2305
- Barnum, D.W.¹

35
- 0003972881
- John Wiley & Sons: New York
- Hine, J. Structural Effects on Equilibria in Organic Chemistry; John Wiley & Sons: New York, 1975; pp 38-46.
- (1975) Structural Effects on Equilibria in Organic Chemistry , pp. 38-46
- Hine, J.¹

36
- 1942491935
- note
- 2OH group of hydroxyacetone.

37
- 0003603853
- Hine, J.; Mahone, L. G.; Liotta, C. L. J. Am. Chem. Soc. 1967, 89, 5911-5920.
- (1967) J. Am. Chem. Soc. , vol.89 , pp. 5911-5920
- Hine, J.¹ Mahone, L.G.² Liotta, C.L.³

38
- 33947306589
- Marcus, R. A. J. Phys. Chem. 1968, 72, 891-899.
- (1968) J. Phys. Chem. , vol.72 , pp. 891-899
- Marcus, R.A.¹

39
- 0000989255
- Marcus, R. A. J. Am. Chem. Soc. 1969, 91, 7224-7225.
- (1969) J. Am. Chem. Soc. , vol.91 , pp. 7224-7225
- Marcus, R.A.¹

40
- 0035543101
- Richard, J. P.; Amyes, T. L.; Toteva, M. M. Acc. Chem. Res. 2001, 34, 981-988.
- (2001) Acc. Chem. Res. , vol.34 , pp. 981-988
- Richard, J.P.¹ Amyes, T.L.² Toteva, M.M.³

41
- 0003972881
- John Wiley & Sons: New York
- Hine, J. Structural Effects on Equilibria in Organic Chemistry; John Wiley & Sons: New York, 1975; pp 270-276.
- (1975) Structural Effects on Equilibria in Organic Chemistry , pp. 270-276
- Hine, J.¹

42
- 0003972881
- John Wiley & Sons: New York
- Hine, J. Structural Effects on Equilibria in Organic Chemistry; John Wiley & Sons: New York, 1975; pp 181-184.
- (1975) Structural Effects on Equilibria in Organic Chemistry , pp. 181-184
- Hine, J.¹

43
- 0000590650
- Castejon, H. J.; Wiberg, K. B. J. Org. Chem. 1998, 63, 3937-3942.
- (1998) J. Org. Chem. , vol.63 , pp. 3937-3942
- Castejon, H.J.¹ Wiberg, K.B.²

44
- 0021471746
- Richard, J. P. J. Am. Chem. Soc. 1984, 106, 4926-4936.
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 4926-4936
- Richard, J.P.¹

45
- 0142126747
- Wise, E. L.; Yew, W. S.; Gerlt, J. A.; Rayment, I. Biochemistry 2003, 42, 12133-12142.
- (2003) Biochemistry , vol.42 , pp. 12133-12142
- Wise, E.L.¹ Yew, W.S.² Gerlt, J.A.³ Rayment, I.⁴

46
- 0346726109
- Garcia-Viloca, M.; Gao, J.; Karplus, M.; Truhlar, D. G. Science 2004, 303, 186-195.
- (2004) Science , vol.303 , pp. 186-195
- Garcia-Viloca, M.¹ Gao, J.² Karplus, M.³ Truhlar, D.G.⁴

47
- 0033577302
- Alhambra, C.; Gao, J.; Corchado, J. C.; Villa, J.; Truhlar, D. G. J. Am. Chem. Soc. 1999, 121, 2253-2258.
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 2253-2258
- Alhambra, C.¹ Gao, J.² Corchado, J.C.³ Villa, J.⁴ Truhlar, D.G.⁵

48
- 0034686678
- Liu, H.; Zhang, Y.; Yang, W. J. Am. Chem. Soc. 2000, 122, 6560-6570.
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 6560-6570
- Liu, H.¹ Zhang, Y.² Yang, W.³

49
- 0002347758
- Rappoport, Z., Ed.; John Wiley and Sons: Chichester
- Keeffe, J. R.; Kresge, A. J. In The Chemistry of Enols; Rappoport, Z., Ed.; John Wiley and Sons: Chichester, 1990; pp 399-480.
- (1990) The Chemistry of Enols , pp. 399-480
- Keeffe, J.R.¹ Kresge, A.J.²

50
- 1942491892
- Page, M. I., Williams, A., Eds.; Royal Society of Chemistry: London
- Richard, J. P. In Enzyme Mechanisms; Page, M. I., Williams, A., Eds.; Royal Society of Chemistry: London, 1987; pp 298-316.
- (1987) Enzyme Mechanisms , pp. 298-316
- Richard, J.P.¹

51
- 0032538627
- Warshel, A. J. Biol. Chem. 1998, 273, 27035-27038.
- (1998) J. Biol. Chem. , vol.273 , pp. 27035-27038
- Warshel, A.¹

52
- 0032500555
- Cannon, W. R.; Benkovic, S. J. J. Biol. Chem. 1998, 273, 26257-26260.
- (1998) J. Biol. Chem. , vol.273 , pp. 26257-26260
- Cannon, W.R.¹ Benkovic, S.J.²

53
- 0028854341
- Scheiner, S.; Kar, T. J. Am. Chem. Soc. 1995, 117, 6970-6975.
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 6970-6975
- Scheiner, S.¹ Kar, T.²

54
- 0029040169
- Warshel, A.; Papazyan, A.; Kollman, P. A. Science 1995, 269, 102-104.
- (1995) Science , vol.269 , pp. 102-104
- Warshel, A.¹ Papazyan, A.² Kollman, P.A.³

55
- 0030462453
- Warshel, A.; Papazyan, A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 13665-13670.
- (1996) Proc. Natl. Acad. Sci. U.S.A. , vol.93 , pp. 13665-13670
- Warshel, A.¹ Papazyan, A.²

56
- 0030090490
- Guthrie, J. P. Chem. Biol. 1996, 3, 163-170.
- (1996) Chem. Biol. , vol.3 , pp. 163-170
- Guthrie, J.P.¹

57
- 0000962819
- Patrick, J. S.; Yang, S. S.; Cooks, R. G. J. Am. Chem. Soc. 1996, 118, 231-232.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 231-232
- Patrick, J.S.¹ Yang, S.S.² Cooks, R.G.³

58
- 0032522105
- Price, W. D.; Jockusch, R. A.; Williams, E. R. J. Am. Chem. Soc. 1998, 120, 3474-3484.
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 3474-3484
- Price, W.D.¹ Jockusch, R.A.² Williams, E.R.³

59
- 0037826844
- Williams, G.; Maziarz, E. P.; Amyes, T. L.; Wood, T. D.; Richard, J. P. Biochemistry 2003, 42, 8354-8361.
- (2003) Biochemistry , vol.42 , pp. 8354-8361
- Williams, G.¹ Maziarz, E.P.² Amyes, T.L.³ Wood, T.D.⁴ Richard, J.P.⁵

60
- 0033580678
- Jordan, F.; Li, H.; Brown, A. Biochemistry 1999, 38, 6369-6373.
- (1999) Biochemistry , vol.38 , pp. 6369-6373
- Jordan, F.¹ Li, H.² Brown, A.³

61
- 0030009782
- Larsen, T. M.; Wedekind, J. E.; Rayment, I.; Reed, G. H. Biochemistry 1996, 35, 4349-4358.
- (1996) Biochemistry , vol.35 , pp. 4349-4358
- Larsen, T.M.¹ Wedekind, J.E.² Rayment, I.³ Reed, G.H.⁴

62
- 0016624901
- Meister, A., Ed.; John Wiley and Sons
- Jencks, W. P. In Advances in Enzymology and Related Areas of Molecular Biology; Meister, A., Ed.; John Wiley and Sons: 1975; Vol. 43, pp 219-410.
- (1975) Advances in Enzymology and Related Areas of Molecular Biology , vol.43 , pp. 219-410
- Jencks, W.P.¹

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