Formation and stability of organic zwitterions in aqueous solution: Enolates of the amino acid glycine and its derivatives

Journal of the American Chemical Society

Volumn 122, Issue 39, 2000, Pages 9373-9385

  Rios, Ana ^a,b   Amyes, Tina L ^a   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

AMMONIUM DERIVATIVE; AMPHOLYTE; BETAINE; BETAINE METHYL ESTER; DEUTERIUM; GLYCINE; GLYCINE DERIVATIVE; GLYCINE METHYL ESTER; UNCLASSIFIED DRUG;

ACIDITY; AQUEOUS SOLUTION; ARTICLE; CONFORMATIONAL TRANSITION; ELECTRICITY; EQUILIBRIUM CONSTANT; PROTEIN PROCESSING; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; STRUCTURE ACTIVITY RELATION;

EID: 0034605454     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001749c     Document Type: Article

References (100)

1. Bada, J. L.; Kvenvolden, K. A.; Peterson, E. Nature 1973, 245, 308-310.
2. Helfman, P. M.; Bada, J. L. Proc. Nat. Acad. Sci. U.S.A. 1975, 72, 297-281.
3. Man, E. H.; Sandhouse, M. E.; Burg, J.; Fisher, G. H. Science 1983, 220, 1407-1408.
4. Helfman, P. M.; Bada, J. L. Nature 1976, 262, 279-281.
5. Masters, P. M.; Bada, J. L.; Zigler, J. S. Nature 1977, 202, 71-73.
6. Zhao, M.; Bada, J. L.; Ahern, T. J. Bioorg. Chem. 1989, 17, 36-40.
7. Steinberg, S. M.; Masters, P. M.; Bada, J. L. Bioorg. Chem. 1984, 12, 349-55.
8. Stroud, E. D.; Fife, D. J.; Smith, G. G. J. Org. Chem. 1983, 48, 5368-5369.
9. Baum, R.; Smith, G. G. J. Am. Chem. Soc. 1986, 108, 7325-7327.
10. Smith, G. G.; Evans, R. C.; Baum, R. J. Am. Chem. Soc. 1986, 108, 7327-7332.
11. Smith, G. G.; Reddy, G. V. J. Org. Chem. 1989, 54, 4529-4535.
12. Kemp, D. S. In The Peptides; Undenfriend, S., Meienhofer, J., Eds.; Academic Press: New York, 1979; Vol. 1.
13. Amyes, T. L.; Richard, J. P. J. Am. Chem. Soc. 1992, 114, 10297-10302.
14. Amyes, T. L.; Richard, J. P. J. Am. Chem. Soc. 1996, 118, 3129-3141.
15. Richard, J. P.; Williams, G.; Gao, J. J. Am. Chem. Soc. 1999, 121, 715-726.
16. Nagorski, R. W.; Mizerski, T.; Richard, J. P. J. Am. Chem. Soc. 1995, 117, 4718-4719. Richard, J. P.; Nagorski, R. W. J. Am. Chem. Soc. 1999, 121, 4763-4770.
17. Nagorski, R. W.; Mizerski, T.; Richard, J. P. J. Am. Chem. Soc. 1995, 117, 4718-4719. Richard, J. P.; Nagorski, R. W. J. Am. Chem. Soc. 1999, 121, 4763-4770.
18. Cardinale, G. J.; Abeles, R. H. Biochemistry 1968, 7, 3970-3978.
19. Rudnick, G.; Abeles, R. H. Biochemistry 1975, 14, 4515-4522.
20. Belasco, J. G.; Albery, W. J.; Knowles, J. R. J. Am. Chem. Soc. 1983, 105, 2475-2477.
21. Tanner, M. E.; Gallo, K. A.; Knowles, J. R. Biochemistry 1993, 32, 3998-4006.
22. Gallo, K. A.; Tanner, M. E.; Knowles, J. R. Biochemistry 1993, 32, 3991-3997.
23. Albery, W. J.; Knowles, J. R. Biochemistry 1986, 25, 2572-2577.
24. Cirilli, M.; Zheng, R.; Scapin, G.; Blanchard, J. S. Biochemistry 1998, 37, 16452-16458.
25. Kou, C. W.; Blanchard, J. S. Biochemistry 1999, 38, 4416-4422.
26. Rios, A.; Richard, J. P. J. Am. Chem. Soc. 1997, 119, 8375-8376.
27. Williams, G. Ph.D. Thesis, University at Buffalo, SUNY, 1998.
28. Renshaw, R. R.; Hotchkiss, H. T. J. Am. Chem. Soc. 1926, 48, 2698-2702.
29. Glasoe, P. K.; Long, F. A. J. Phys. Chem. 1960, 64, 188-190.
30. Covington, A. K.; Robinson, R. A.; Bates, R. G. J. Phys. Chem. 1966, 70, 3820-3824.
31. Albert, A.; Serjeant, E. P. The Determination of Ionization Constants, 3rd ed.; Chapman and Hall: London, 1984.
32. (a) Halkides, C. J.; Frey, P. A.; Tobin, J. B. J. Am. Chem. Soc. 1993, 115, 3332-3333.
33. (b) Tobin, J. B.; Frey, P. A. J. Am. Chem. Soc. 1996, 118, 12253-12260.
34. Alston, W. C.; Haley, K.; Kanski, R.; Murray, C. J.; Pranata, J. J. Am. Chem. Soc. 1996, 118, 6562-6569.
35. 3D = 0.90 for the isotope effect on the hydroxide-catalyzed hydrolysis of trideuterated ethyl acetate in water: Bender, M. L.; Feng, M. S. J. Am. Chem. Soc. 1960, 82, 6318-6321.
36. B with decreasing catalyst basicity.
37. -1) on [3-quinuclidinol] is due to general base catalysis of enolization rather than a specific salt or medium effect. We consider it to be tentative, because we have no data for specific salt and medium effects on the deprotonation of these glycine derivatives.
38. Smith, G. G.; Sivakua, T. J. Org. Chem. 1983, 48, 627-634.
39. Bada, J. L. J. Am. Chem. Soc. 1972, 94, 1371-1373.
40. HO = 2.4 for formation of very unstable carbanions, for which lyoxide-catalyzed exchange is limited by solvent reorganization that exchanges the hydron of substrate with a labeled hydron from solvent: Gold, V.; Grist, S. J. Chem. Soc., Perkin Trans. 2 1972, 89-95. Kresge, A. J.; O'Ferrall, R. A. M.; Powell, M. F. In Isotopes in Organic Chemistry; Buncel, E., Lee, C. C., Eds.; Elsevier: New York, 1987; Vol. 7. Therefore, we use the average of the these values as the estimated secondary solvent deuterium isotope effect.
41. HO = 2.4 for formation of very unstable carbanions, for which lyoxide-catalyzed exchange is limited by solvent reorganization that exchanges the hydron of substrate with a labeled hydron from solvent: Gold, V.; Grist, S. J. Chem. Soc., Perkin Trans. 2 1972, 89-95. Kresge, A. J.; O'Ferrall, R. A. M.; Powell, M. F. In Isotopes in Organic Chemistry; Buncel, E., Lee, C. C., Eds.; Elsevier: New York, 1987; Vol. 7. Therefore, we use the average of the these values as the estimated secondary solvent deuterium isotope effect.
42. Jencks, W. P. J. Am. Chem. Soc. 1972, 94, 4731-4732.
43. 83
44. (a) Bell, R. P. The Proton in Chemistry, 2nd ed.; Cornell University Press: Ithaca, NY, 1973; p 150.
45. (b) Keeffe, J. R.; Kresge, A. J. In The Chemistry of Enols; Rappoport, Z., Ed.; John Wiley and Sons: Chichester, 1990; pp 399-480.
46. (c) Carey, A. R. E.; Al-Quatami, S.; More O'Ferrall, R. A.; Murray, B. A. J. Chem. Soc., Chem. Commun. 1988, 1097-1098.
47. (d) Chiang, Y.; Kresge, A. J.; Morimoto, H.; Williams, P. G. J. Am. Chem. Soc. 1992, 114, 3981-3982.
48. H is marginally smaller than that for protonation of the slightly more unstable enolate of acetone.
49. See footnote 48 in: Argyrou, A.; Washabaugh, M. W. J. Am. Chem. Soc. 1999, 121, 12054-12062.
50. Pucker, Y. Chem. Ind. 1959, 1383-1384.
51. Giese, K.; Kaatze, U.; Pottel, R. J. Phys. Chem. 1970, 74, 3718-3725.
52. Kaatze, U. J. Chem. Eng. Data 1989, 34, 371-374.
53. Kaatze, U.; Pottel, R.; Schumacher, A. J. Phys. Chem. 1992, 96, 6017-6020.
54. a + log p) - 7.918.
55. Bernasconi, C. F.; Moreira, J. A.; Huang, L. L.; Kittredge, K. W. J. Am. Chem. Soc. 1999, 121, 1674-1680.
56. -11 M (Figure 2).
57. Hine, J. In Structural Effects on Equilibria in Organic Chemistry; Wiley: New York, 1975; p 98.
58. Kirkwood, J. G.; Westheimer, F. H. J. Chem. Phys. 1938, 6, 506-512.
59. Kirkwood, J. G.; Westheimer, F. H. J. Chem. Phys. 1938, 6, 512-517.
60. 2OH was taken from: Hine, J.; Kokesh, F. C. J. Am. Chem. Soc. 1970, 92, 4383-4388.
61. A simple electrostatic treatment of the interactions between a carbanion and polar substituents predicts an attenuation factor of 4.0 for the insertion of a methylene group between interacting charges and dipoles at adjacent atoms (ref 53, p 96). Smaller attenuation factors of 2-3 are observed in cases where the initial separation of interacting charges is larger (ref 53, pp 161-162).
62. Wiberg, K. B.; Castejon, H. J. Org. Chem. 1995, 60, 6322-6334.
63. 27 in the preliminary communication of this work.
64. Thibblin, A. J. Am. Chem. Soc. 1984, 106, 183-186.
65. Chwang, W. K.; Eliason, R.; Kresge, A. J. J. Am. Chem. Soc. 1977, 99, 805-808.
66. Richard, J. P. J. Am. Chem. Soc. 1984, 106, 4926-4936.
67. Halvarsson, T.; Bergman, N. A. J. Org. Chem. 1991, 56, 251-254.
68. 2O (Table 1) by quinuclidine, 3-quinuclidinol, and 3-chloroquinuclidine give Brønsted coefficients of β = 0.48 and β = 0.96, respectively.
69. Hupe, D. J.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 451-464.
70. Williams, A. Adv. Phys. Org. Chem. 1992, 27, 1-55.
71. Kresge, A. J. Chem. Soc. Rev. 1973, 2, 475-503.
72. Jencks, W. P.; Brant, S. R.; Gandler, J. R.; Fendrich, G.; Nakamura, C. J. Am. Chem. Soc. 1982, 104, 7045-7051.
73. Washabaugh, M. W.; Jencks, W. P. J. Am. Chem. Soc. 1989, 111, 683-692.
74. Bernasconi, C. F. Acc. Chem. Res. 1992, 25, 9-16.
75. Bernasconi, C. F. Tetrahedron 1985, 41, 3219-3234.
76. Bernasconi, C. F. Acc. Chem. Res. 1987, 20, 301-308.
77. Bernasconi, C. F. Adv. Phys. Org. Chem. 1992, 27, 119-238.
78. Richard, J. P.; Toteva, M. M.; Crugeiras, J. J. Am. Chem. Soc. 2000, 122, 1664-1674.
79. Lee, I.; Chung, D. S.; Jung, H. J. Tetrahedron 1994, 50, 7981-7986.
80. Richard, J. P. Tetrahedron 1995, 51, 1535-1573.
81. Richard, J. P.; Amyes, T. L.; Williams, K. B. Pure Appl. Chem. 1998, 70, 2007-2014.
82. Richard, J. P. J. Org. Chem. 1994, 59, 25-29.
83. Richard, J. P. J. Am. Chem. Soc. 1989, 111, 1455-1465. Amyes, T. L.; Stevens, I. W.; Richard, J. P. J. Org. Chem. 1993, 58, 6057-6066.
84. Richard, J. P. J. Am. Chem. Soc. 1989, 111, 1455-1465. Amyes, T. L.; Stevens, I. W.; Richard, J. P. J. Org. Chem. 1993, 58, 6057-6066.
85. (a) Fisher, L. M.; Albery, W. J.; Knowles, J. R. Biochemistry 1986, 25, 2529-2537.
86. (b) Belasco, J. G.; Albery, W. J.; Knowles, J. R. Biochemistry 1986, 25, 2552-2558.
87. Glavas, S.; Tanner, M. E. Biochemistry 1999, 38, 4106-4113.
88. 80a
89. Jencks, W. P.; Regenstein, J. In Handbook of Biochemistry and Molecular Biology, Physical and Chemical Data, 3rd ed.; Fasman, G. D., Ed.; CRC Press: Cleveland, OH, 1976; Vol. 1; pp 305-351.
90. Hammes, G. G.; Schimmel, P. R. The Enzymes (3rd ed.) 1970, 2, 67-114.
91. Gerlt, J. A.; Gassman, P. G. Biochemistry 1993, 32, 11943-11952.
92. Gerlt, J. A.; Kozarich, J. W.; Kenyon, G. L.; Gassman, P. G. J. Am. Chem. Soc. 1991, 113, 9667-9669.
93. Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1992, 114, 5928-5934.
94. Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552-11568.
95. Richard, J. P. Biochemistry 1998, 37, 4305-4309.
96. Patrick, J. S.; Yang, S. S.; Cooks, R. G. J. Am. Chem. Soc. 1996, 118, 231-232.
97. Price, W. D.; Jockusch, R. A.; Williams, E. R. J. Am. Chem. Soc. 1998, 120, 3474-3484.
98. Jencks, W. P. In Advances in Enzymology and Related Areas of Molecular Biology; Meister, A., Ed.; John Wiley and Sons: New York, 1975; Vol. 43, pp 219-410.
99. Keeffe, J. R.; Kresge, A. J.; Yin, Y. J. Am. Chem. Soc. 1988, 110, 8201-8206.
100. Jordan, F.; Li, H.; Brown, A. Biochemistry 1999, 38, 6369-6373.