Alkaline phosphatase mono- and diesterase reactions: Comparative transition state analysis

Journal of the American Chemical Society

Volumn 128, Issue 4, 2006, Pages 1293-1303

  Zalatan, Jesse G ^a   Herschlag, Daniel ^a,b  

^a STANFORD UNIVERSITY   (United States)

^b STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CATALYSIS; CHEMICAL REACTIONS; ENZYMES; HYDROLYSIS; OPTIMIZATION; SOLUTIONS;

ALKALINE PHOSPHATASE (AP); COMPARATIVE TRANSITION STATE ANALYSIS; ENZYME-CATALYZED PHOSPHORYL TRANSFER REACTIONS; PHOSPHATE MONOESTERS;

ENZYME KINETICS;

ALKALINE PHOSPHATASE; BACTERIAL ENZYME; ESTERASE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENERGY; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ESCHERICHIA COLI; HYDROLYSIS; NONHUMAN; REACTION ANALYSIS;

ALKALINE PHOSPHATASE; CATALYSIS; ESCHERICHIA COLI; HYDROLYSIS; KINETICS; PHOSPHORIC ACID ESTERS; THERMODYNAMICS;

EID: 31944441501     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja056528r     Document Type: Article

References (102)

1. Coleman, J. E. Annu. Rev. Biophys. Biomol. Struct. 1992, 21, 441-483.
2. O'Brien, P. J.; Herschlag, D. Biochemistry 2001, 40, 5691-5699.
3. Jensen, R. A. Annu. Rev. Microbiol. 1976, 30, 409-425.
4. O'Brien, P. J.; Herschlag, D. Chem. Biol. 1999, 6, R91-R105.
5. Palmer, D. R. J.; Garrett, J. B.; Sharma, V.; Meganathan, R.; Babbitt, P. C.; Gerlt, J. A. Biochemistry 1999, 38, 4252-4258.
6. Penning, T. M.; Jez, J. M. Chem. Rev. 2001, 101, 3027-3046.
7. Copley, S. D. Curr. Opin. Chem. Biol. 2003, 7, 265-272.
8. James, L. C.; Tawfik, D. S. Trends Biochem. Sci. 2003, 28, 361-368.
9. Galperin, M. Y.; Bairoch, A.; Koonin, E. V. Protein Sci 1998, 7, 1829-1835.
10. Galperin, M. Y.; Jedrzejas, M. J. Proteins 2001, 45, 318-324.
11. Gijsbers, R.; Ceulemans, H.; Stalmans, W.; Bollen, M. J. Biol Chem. 2001, 276, 1361-1368.
12. Kim, E. E.; Wyckoff, H. W. J. Mol. Biol. 1991, 218, 449-464.
13. Holtz, K. M.; Stec, B.; Kantrowitz, E. R. J. Biol. Chem. 1999, 274, 8351-8354.
14. Beese, L. S.; Steitz, T. A. EMBO J. 1991, 10, 25-33.
15. Steitz, T. A. J. Biol. Chem. 1999, 274, 17395-17398.
16. Wilcox, D. E. Chem. Rev. 1996, 96, 2435-2458.
17. Strater, N.; Lipscomb, W. N.; Klabunde, T.; Krebs, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2024-2055.
18. Polanyi, M. Z. Elektrochem. Z. 1921, 27, 142.
19. Pauling, L. Chem. Eng. News 1946, 24, 1375-1377.
20. Wolfenden, R. Acc. Chem. Res. 1972, 5, 10-18.
21. Lienhard, G. E. Science 1973, 180, 149-154.
22. Jencks, W. P. Catalysis in Chemistry and Enzymology; Dover Publications: New York, 1987.
23. Weiss, P. M.; Cleland, W. W. J. Am. Chem. Soc. 1989, 111, 1928-1929.
24. Hollfelder, F.; Herschlag, D. Biochemistry 1995, 34, 12255-12264.
25. O'Brien, P. J.; Herschlag, D. J. Am. Chem. Soc. 1999, 121, 11022-11023.
26. Holtz, K. M.; Catrina, I. E.; Hengge, A. C.; Kantrowitz, E. R. Biochemistry 2000, 59, 9451-9458.
27. O'Brien, P. J.; Herschlag, D. Biochemistry 2002, 41, 3207-3225.
28. Nikolic-Hughes, I.; Rees, D. C.; Herschlag, D. J. Am. Chem. Soc. 2004, 126, 11814-11819.
29. Kirby, A. J.; Jencks, W. P. J. Am. Chem. Soc. 1965, 87, 3209-3216.
30. Kirby, A. J.; Varvoglis, A. G. J. Am. Chem. Soc. 1967, 89, 415-423.
31. Hengge, A. C.; Edens, W. A.; Elsing, H. J. Am. Chem. Soc. 1994, 116, 5045-5049.
32. Thatcher, G. R. J.; Kluger, R. Adv. Phys. Org. Chem. 1989, 25, 99-265.
33. Hengge, A. C.; Onyido, I. Curr. Org. Chem. 2005, 9, 61-74.
34. Kirby, A. J.; Younas, M. J. Chem. Soc. B 1970, 1165-1172.
35. Kirby, A. J.; Younas, M. J. Chem. Soc. B 1970, 510-513.
36. Hengge, A. C.; Cleland, W. W. J. Am. Chem. Soc. 1991, 113, 5835-5841.
37. Hengge, A. C.; Tobin, A. E.; Cleland, W. W. J. Am. Chem. Soc. 1995, 117, 5919-5926.
38. More O'Ferrall, R. A. J. Chem. Soc. B 1970, 274-277.
39. Jencks, W. P. Chem. Rev. 1972, 72, 705-718.
40. Breslow, R.; Katz, I. J. Am. Chem. Soc. 1968, 90, 7376-7377.
41. Hall, A. D.; Williams, A. Biochemistry 1986, 25, 4784-4790.
42. Han, R.; Coleman, J. E. Biochemistry 1995, 34, 4238-4245.
43. Jencks, W. P. Chem. Rev. 1985, 85, 511-527.
44. Herschlag, D.; Jencks, W. P. Biochemistry 1990, 29, 5172-5179.
45. Herschlag, D.; Piccirilli, J. A.; Cech, T. R. Biochemistry 1991, 30, 4844-4854.
46. Zhang, Y. L.; Hollfelder, F.; Gordon, S. J.; Chen, L.; Keng, Y. F.; Wu, L.; Herschlag, D.; Zhang, Z. Y. Biochemistry 1999, 38, 12111-12123.
47. Williams, A. Adv. Phys. Org. Chem. 1992, 27, 1-55.
48. Ig.
49. Chin, J.; Banaszczyk, M.; Jubian, V.; Zou, X. J. Am. Chem. Soc. 1989, 111, 186-190.
50. Williams, N. H.; Cheung, W.; Chin, J. J. Am. Chem. Soc. 1998, 120, 8079-8087.
51. Liao, X. M.; Anjaneyulu, P. S. R.; Curley, J. F.; Hsu, M.; Boehringer, M.; Caruthers, M. H.; Piccirilli, J. A. Biochemistry 2001, 40, 10911-10926.
52. Ba-Saif, S. A.; Davis, A. M.; Williams, A. J. Org. Chem. 1989, 54, 5483-5486.
53. Williams, N. H.; Wyman, P. Chem. Commun. 2001, 1268-1269.
54. Leffler, J. E. Science 1953, 117, 340-341.
55. Williams, A. Acc. Chem. Res. 1984, 17, 425-430.
56. Bourne, N.; Williams, A. J. Org. Chem. 1984, 49, 1200-1204.
57. Jencks, W. P.; Regenstein, J. Ionization Constants of Acids and Bases. In Handbook of Biochemistry and Molecular Biology; Fasman, G. D., Ed.; CRC: Cleveland, OH, 1976.
58. Bolton, P. D.; Ellis, J.; Hall, F. M. J. Chem. Soc. B 1970, 1252-1255.
59. Chaidaroglou, A.; Brezinski, D. J.; Middleton, S. A.; Kantrowitz, E. R. Biochemistry 1988, 27, 8338-8343.
60. Bernasconi, C. F. Adv. Phys. Org. Chem. 1992, 27, 119-238.
61. 25,28
62. Rajca, A.; Rice, J. E.; Streitwieser, A.; Schaefer, H. F. J. Am. Chem. Soc. 1987, 109, 4189-4192.
63. Horn, H.; Ahlrichs, R. J. Am. Chem. Soc. 1990, 112, 2121-2124.
64. Mildvan, A. S. Proteins 1997, 29, 401-416.
65. Hengge, A. C. Acc. Chem. Res. 2002, 35, 105-112.
66. Grzyska, P. K.; Kim, Y.; Jackson, M. D.; Hengge, A. C.; Denu, J. M. Biochemistry 2004, 43, 8807-8814.
67. McCain, D. F.; Grzyska, P. K.; Wu, L.; Hengge, A. C.; Zhang, Z. Y. Biochemistry 2004, 43, 8256-8264.
68. Hengge, A. C.; Martin, B. L. Biochemistry 1997, 36, 10185-10191.
69. Hoff, R. H.; Mertz, P.; Rusnak, F.; Hengge, A. C. J. Am. Chem. Soc. 1999, 121, 6382-6390.
70. Du, X. L.; Black, G. E.; Lecchi, P.; Abramson, F. P.; Sprang, S. R. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 8858-8863.
71. Kim, K.; Cole, P. A. J. Am. Chem. Soc. 1997, 119, 11096-11097.
72. Kim, K.; Cole, P. A. J. Am. Chem. Soc. 1998, 120, 6851-6858.
73. Paoli, P.; Cirri, P.; Camici, L.; Manao, G.; Cappugi, G.; Moneti, G.; Pieraccini, G.; Camici, G.; Ramponi, G. Biochem. J. 1997, 327, 177-184.
74. Gerratana, B.; Frey, P. A.; Cleland, W. W. Biochemistry 2001, 40, 2972-2977.
75. Cassano, A. G.; Anderson, V. E.; Harris, M. E. Biochemistry 2004, 43, 10547-10559.
76. Caldwell, S. R.; Raushel, F. M.; Weiss, P. M.; Cleland, W. W. Biochemistry 1991, 30, 7444-7450.
77. Caldwell, S. R.; Newcomb, J. R.; Schlecht, K. A.; Raushel, F. M. Biochemistry 1991, 30, 7438-7444.
78. Hong, S. B.; Raushel, F. M. Biochemistry 1996, 35, 10904-10912.
79. Khan, S. A.; Kirby, A. J. J. Chem. Soc. B 1970, 1172-1182.
80. Liu, S. J.; Lu, Z. B.; Jia, Y.; Dunaway-Mariano, D.; Herzberg, O. Biochemistry 2002, 41, 10270-10276.
81. Choe, J. Y.; Iancu, C. V.; Fromm, H. J.; Honzatko, R. B. J. Biol. Chem. 2003, 278, 16015-16020.
82. Lahiri, S. D.; Zhang, G. F.; Dunaway-Mariano, D.; Allen, K. N. Science 2003, 299, 2067-2071.
83. Leiros, I.; McSweeney, S.; Hough, E. J. Mol. Biol. 2004, 339, 805-820.
84. Blackburn, G. M.; Williams, N. H.; Gamblin, S. J.; Smerdon, S. J. Science 2003, 301, 1184c.
85. Allen, K. N.; Dunaway-Mariano, D. Science 2003, 301, 1184d.
86. Yarnell, A. Chem. Eng. News 2003, 81, 30-31.
87. Webster, C. E. J. Am. Chem. Soc. 2004, 126, 6840-6841.
88. Tremblay, L. W.; Zhang, G.; Dai, J.; Dunaway-Mariano, D.; Allen, K. N. J. Am. Chem. Soc. 2005, 127, 5298-5299.
89. Berti, P. J.; Tanaka, K. S. E. Adv. Phys. Org. Chem. 2002, 37, 239-314.
90. Schramm, V. L. Acc. Chem. Res. 2003, 36, 588-596.
91. Amyes, T. L.; Jencks, W. P. J. Am. Chem. Soc. 1989, 111, 7900-7909.
92. Banait, N. S.; Jencks, W. P. J. Am. Chem. Soc. 1991, 113, 7951-7958.
93. O'Brien, P. J.; Herschlag, D. J. Am. Chem. Soc. 1998, 120, 12369-12370.
94. Nikolic-Hughes, I.; O'Brien, P. J.; Herschlag, D. J. Am. Chem. Soc. 2005, 127, 9314-9315.
95. Cassano, A. G.; Anderson, V. E.; Harris, M. E. J. Am. Chem. Soc. 2002, 124, 10964-10965.
96. Lad, C.; Williams, N. H.; Wolfenden, R. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 5607-5610.
97. Gill, S. C.; von Hippel, P. H. Anal. Biochem. 1989, 182, 319-326.
98. 102 does not significantly alter the results of this analysis and does not affect the conclusions drawn.
99. Postmus, C.; Magnusson, L. B.; Craig, C. A. Inorg. Chem. 1966, 5, 1154-1157.
100. a of the phosphate ester (eq 5) was determined for phosphate monoesters. We assume that this correlation also holds for diesters.
101. Herschlag, D.; Jencks, W. P. J. Am. Chem. Soc. 1989, 111, 7587-7596.
102. Baes, C. F., Jr.; Mesmer, R. E. The Hydrolysis of Cations; Wiley: New York, 1976.