Elucidation of enzyme mechanisms using fluorinated substrate analogues

Bioorganic Chemistry

Volumn 32, Issue 5, 2004, Pages 393-437

  Pongdee, Rongson ^a   Liu, Hung Wen ^a  

^a UNIVERSITY OF TEXAS   (United States)

Author keywords

Fluorinated substrates

Indexed keywords

ANTIINFECTIVE AGENT; ENZYME INHIBITOR; FLUORINE DERIVATIVE; FOSFOMYCIN; GLYCOSIDASE INHIBITOR; GLYCOSIDE; HYDROGEN; HYDROXYL GROUP;

DRUG STRUCTURE; ENZYME MECHANISM; ENZYME SUBSTRATE; FLUORINATION; HUMAN; MOLECULAR PROBE; NONHUMAN; PRIORITY JOURNAL; SHORT SURVEY;

EID: 4644328108     PISSN: 00452068     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bioorg.2004.06.012     Document Type: Review

References (130)

1. C. Walsh Tetrahedron 38 1982 871 909
2. C. Walsh A. Meister Advances in Enzymology vol. 55 1983 John Wiley & Sons New York 197 289
3. D. O'Hagan, and H.S. Rzepa J. Chem. Soc., Chem. Commun. 1997 645 652
4. A. Stabel, L. Dasaradhi, D. O'Hagan, and J.P. Rabe Langmuir 11 1995 1427 1430
5. P.M. Dewick Nat. Prod. Rep. 19 2002 181 222
6. T. Kuzuyama, and H. Seto Nat. Prod. Rep. 20 2003 171 183
7. J.W. Cornforth, R.H. Cornforth, G. Popjak, and L. Yengoyan J. Biol. Chem. 241 1966 3970 3987
8. C.D. Poulter, and H.C. Rilling Acc. Chem. Res. 11 1978 307 313
9. H.C. Rilling, and K. Bloch J. Biol. Chem. 234 1959 1424 1432
10. J.W. Cornforth, and G. Popjak Tetrahedron Lett. 1959 29 35
11. C.D. Poulter, and H.C. Rilling Biochemistry 15 1976 1079 1083
12. C.D. Poulter, and D.M. Satterwhite Biochemistry 16 1977 5470 5478
13. Y. Okamoto, T. Inukai, and H.C. Brown J. Am. Chem. Soc. 80 1958 4969 4972
14. C.D. Poulter, J.C. Argyle, and E.A. Mash J. Am. Chem. Soc. 99 1977 957 959
15. C.D. Poulter, J.C. Argyle, and E.A. Mash J. Biol. Chem. 253 1978 7227 7233
16. G. Popjak, and J.W. Cornforth Biochem. J. 101 1966 553 568
17. J.E. Reardon, and R.H. Abeles J. Am. Chem. Soc. 107 1985 4078 4079
18. M. Muehlbacher, and C.D. Poulter J. Am. Chem. Soc. 107 1985 8307 8308
19. A.S. Narula, A. Rahier, P. Benveniste, P. Place, and C. Anding J. Am. Chem. Soc. 103 1981 2408 2409
20. R.M. Sandifer, M.D. Thompson, R.G. Gaughen, and C.D. Poulter J. Am. Chem. Soc. 104 1982 7376 7378
21. A. Rahier, J.C. Genot, F. Schuber, P. Benveniste, and A.S. Narula J. Biol. Chem. 259 1984 15215 15223
22. A. Rahier, M. Taton, P. Schmitt, P. Benveniste, P. Place, and C. Anging Phytochemistry 24 1985 1223
23. P. Croteau, C.J. Wheeler, R. Aksela, and A.C. Oehlschlager J. Biol. Chem. 261 1986 7257 7263
24. J.E. Reardon, and R.H. Abeles Biochemistry 25 1986 5609 5616
25. M. Muehlbacher, and C.D. Poulter Biochemistry 27 1988 7315 7328
26. C.D. Poulter, M. Muehlbacher, and D.R. Davis J. Am. Chem. Soc. 111 1989 3740 3742
27. I.P. Street, H.R. Coffman, J.A. Baker, and C.D. Poulter Biochemistry 33 1994 4212 4217
28. S.G. Withers, I.P. Street, P. Bird, and D.H. Dolphin J. Am. Chem. Soc. 109 1987 7530 7531
29. S.G. Withers, K. Rupitz, and I.P. Street J. Biol. Chem. 263 1988 7929 7932
30. S.G. Withers, and I.P. Street J. Am. Chem. Soc. 110 1988 8551 8553
31. S.G. Withers, R.A.J. Warren, I.P. Street, K. Rupitz, J.B. Kempton, and R. Aebersold J. Am. Chem. Soc. 112 1990 5887 5889
32. C. Walsh Antibiotics: Actions Origins Resistance 2003 ASM Press Wahington DC 23 50
33. K.S. Anderson, J.A. Sikorski, and K.A. Johnson Biochemistry 27 1988 7395 7406
34. K.S. Anderson, J.A. Sikorski, A.J. Benesi, and K.A. Johnson J. Am. Chem. Soc. 110 1988 6577 6579
35. J.L. Marquardt, E.D. Brown, C.T. Walsh, and K.S. Anderson J. Am. Chem. Soc. 115 1993 10398 10399
36. D.H. Kim, W.J. Lees, and C.T. Walsh J. Am. Chem. Soc. 116 1994 6478 6479
37. E.D. Brown, J.L. Marquardt, J.P. Lee, C.T. Walsh, and K.S. Anderson Biochemistry 33 1994 10638 10645
38. D.H. Kim, W.J. Lees, T.M. Haley, and C.T. Walsh J. Am. Chem. Soc. 117 1995 1494 1502
39. T.P. Begley Nat. Prod. Rep. 13 1996 177
40. J.J. Reddick, R. Nicewonger, and T.P. Begley Biochemistry 40 2001 10095 10102
41. D.W. Grogan, and J.E. Cronan Jr. J. Bacteriol. 158 1984 286 295
42. D.W. Grogan, and J.E. Cronan Jr. J. Bacteriol. 166 1986 872 877
43. M. Monteoliva-Sanchez, A. Ramos-Cormenzana, and N.J. Russell J. Gen. Microbiol. 139 1993 1877 1884
44. A.-Y. Wang, and J.E. Cronan Mol. Microbiol. 11 1994 1009 1017
45. M.S. Glickman, J.S. Cox, and W.R. Jacobs Jr. Mol. Cell 5 2000 717 727
46. E. Lederer Q. Rev. Chem. Soc. 23 1969 453 481
47. J.H. Law Acc. Chem. Res. 4 1971 199 203
48. P.H. Buist, and D.B. Maclean Can. J. Chem. 59 1981 828 838
49. Y. Yuan, and C.E. Barry III Proc. Natl. Acad. Sci. USA 93 1996 12828 12833
50. T. Cohen, G. Herman, T.M. Chapman, and D. Kuhn J. Am. Chem. Soc. 96 1974 5627 5628
51. E.J. Molitor, B.M. Paschal, and H.-w. Liu ChemBioChem 4 2003 1352 1356
52. M.I.S. Lomax, and G.R. Greenberg J. Biol. Chem. 242 1967 109 113
53. M.I.S. Lomax, and G.R. Greenberg J. Biol. Chem. 242 1967 1302 1306
54. D.V. Santi, C.S. McHenry, and H. Sommer Biochemistry 13 1974 471 481
55. R.G. Kallen, and W.P. Jencks J. Biol. Chem. 241 1966 5851 5863
56. S.J. Benkovic, P.A. Benkovic, and D.R. Comfort J. Am. Chem. Soc. 91 1969 5270 5279
57. D.V. Santi, and C.F. Brewer Biochemistry 12 1973 2416 2424
58. A.L. Pogolotti, and D.V. Santi Biochemistry 13 1974 456 466
59. W. Huang, and D.V. Santi J. Biol. Chem. 269 1994 31327 31329
60. C.W. Carreras, and D.V. Santi Annu. Rev. Biochem. 34 1995 721 762
61. D.V. Santi, and A.L. Pogolotti J. Heterocyclic Chem. 8 1971 265 272
62. E.J. Pastore, and M. Friedkin J. Biol. Chem. 237 1962 3802 3809
63. M.G. Kunitani, and D.V. Santi Biochemistry 19 1980 1271 1275
64. J.E. Barrett, D.A. Maltby, D.V. Santi, and P.G. Schultz J. Am. Chem. Soc. 120 1998 449 450
65. L.L. Engel Handbook Physiol. Sect. 7: Endocrinol. 2 1972 467 483
66. P.A. Marcotte, and C.H. Robinson Biochemistry 21 1982 2773 2778
67. W.G. Kelly, D. Judd, and A. Stolee Biochemistry 16 1977 140 145
68. H.-w. Liu, and J.S. Thorson Annu. Rev. Microbiol. 48 1994 223 256
69. X. He, J.S. Thorson, and H.-w. Liu Biochemistry 35 1996 4721 4731
70. Y. Yuan, R.N. Russell, J.S. Thorson, L.-d. Liu, and H.-w. Liu J. Biol. Chem. 267 1992 5868 5875
71. C.-w.T. Chang, X.H. Chen, and H.-w. Liu J. Am. Chem. Soc. 120 1998 9698 9699
72. H. Seto, T. Hidaka, T. Kuzuyama, S. Shibahara, T. Usui, O. Sakanaka, and S. Imai J Antibiot. 44 1991 1286 1288
73. F.J. Hammerschmidt J. Chem. Soc., Perkin Trans. 1 1991 1993 1996
74. P. Liu, K. Murakami, T. Seki, X. He, S.-M. Yeung, T. Kuzuyama, H. Seto, and H.-w. Liu J. Am. Chem. Soc. 123 2001 4619 4620
75. A.G. Prescott, and M.D. Lloyd Nat. Prod. Rep. 17 2000 367 383
76. Z. Zhao, P. Liu, K. Murakami, T. Kuzuyama, H. Seto, and Liu H.-W. Angew. Chem. Int. Ed. 41 2002 4529 4532
77. C. Leriche, X. He, C.-w.T. Chang, and H.-w. Liu J. Am. Chem. Soc. 125 2003 6348 6349
78. T.M. Weigel, L.-d. Liu, and H.-w. Liu Biochemistry 31 1992 2129 2139
79. R.K. Hill, and M.G. Bock J. Am. Chem. Soc. 100 1978 637 639
80. E. Toromanoff, and C.R. Seances Acad. Sci. Ser. C 290 1980 81 84
81. P. Macheroux, J. Schmid, N. Amrhein, and A. Schaller Planta 207 1999 325 334
82. H.G. Floss, D.K. Onderka, and M. Carroll J. Biol. Chem. 247 1972 736 744
83. B. Ganem Tetrahedron 34 1978 3353 3383
84. R.B. Croteau, J.J. Shaskus, B. Renstron, N.M. Felton, D.E. Cane, A. Saito, and C. Chang Biochemistry 24 1985 7077 7085
85. D.E. Cane, R. Iyengar, and M.-S. Shiao J. Am. Chem. Soc. 103 1981 914 931
86. D.E. Cane, A. Saito, R. Croteau, J. Shaskus, and M. Felton J. Am. Chem. Soc. 104 1982 5831 5833
87. D.E. Cane Tetrahedron 36 1980 1109 1159
88. P.A. Bartlett, K.L. McLaren, D.G. Alberg, A. Fassler, R. Nyfeler, C.T. Lauhon, C.B. Grissom, Proc. Soc. Chem. Ind. Pesticides Group Meeting, BCPC Monograph 42 (1989) 155a-170
89. W. Thiel J. Am. Chem. Soc. 103 1981 1413 1420
90. G. Koltzenburg, G. Behrens, and D. Schulte-Frohlinde J. Am. Chem. Soc. 104 1982 7311 7312
91. A. Osborne, R.N.F. Thorneley, C. Abell, and S. Bornemann J. Biol. Chem. 275 2000 35825 35830
92. P.A. Bartlett, U. Maitra, and P.M. Chouinard J. Am. Chem. Soc. 108 1986 8068 8071
93. M.N. Ramjee, J.R. Coggins, T.R. Hawkes, D.J. Lowe, and R.N.F. Thorneley J. Am. Chem. Soc. 113 1991 8566 8567
94. M.N. Ramjee, S. Balasubramanian, C. Abell, J.R. Coggins, G.M. Davies, T.R. Hawkes, D.J. Lowe, and R.N.F. Thorneley J. Am. Chem. Soc. 114 1992 3151 3153
95. C.T. Lauhon, and P.A. Bartlett Biochemistry 33 1994 14100 14108
96. S. Bornemann, M.K. Ramjee, S. Balasubramanian, C. Abell, J.R. Coggins, D.J. Lowe, and R.N.F. Thorneley J. Biol. Chem. 270 1995 22811 22815
97. S. Bornemann, M.-E. Theoclitou, M. Brune, M.R. Webb, R.N.F. Thorneley, and C. Abell Bioorganic Chem. 28 2000 191 204
98. T.M. Weigel, V.P. Miller, and H.-w. Liu Biochemistry 31 1992 2140 2147
99. J.S. Thorson, and H.-w. Liu J. Am. Chem. Soc. 115 1993 7539 7540
100. J.S. Thorson, and H.-w. Liu J. Am. Chem. Soc. 115 1993 12177 12178
101. G.T. Gassner, D.A. Johnson, H.-w. Liu, and D.P. Ballou Biochemistry 35 1996 7752 7761
102. X. He, O. Ploux, and H.-w. Liu Biochemistry 35 1996 16412 16420
103. P.A. Pieper, D.-y. Yang, H.-q. Zhou, and H.-w. Liu J. Am. Chem. Soc. 119 1997 1809 1817
104. C.-W.T. Chang, D.A. Johnson, V. Bandarian, H. Zhou, R. LoBrutto, G.H. Reed, and H.-w. Liu J. Am. Chem. Soc. 122 2000 4239 4240
105. 6 Catalysis 1984 A.R. Liss New York
106. 6 Pyridoxal Phosphate, Chemical, Biochemical, and Medical Aspects 1986 Wiley-Interscience New York Parts A and B
107. P.A. Frey, and S.J. Booker Adv. Protein Chem. 58 2001 1 45
108. P.A. Frey, C.H. Chang, M.D. Ballinger, and G.H. Reed Methods Enzymol. 354 2002 426 435
109. D.A. Johnson, G.T. Gassner, V. Bandarian, F.J. Ruzicka, D.P. Ballou, G.H. Reed, and H.-w. Liu Biochemistry 35 1996 15846 15856
110. D.-y. Yang, Y. Shih, and H.-w. Liu J. Org. Chem. 56 1991 2940 2946
111. A. Carrington, and A.D. McLachlan Introduction to Magnetic Resonance 1967 Harper and Row New York 79 80
112. J.R. Norris, R.A. Uphaus, H.L. Crespi, and J. Katz Proc. Natl. Acad. Sci. USA 68 1971 625 628
113. W.B. Mims Electron Paramagnetic Resonance 1972 Plenum Press New York 263 351
114. T.M. Hallis, and H.-w. Liu J. Am. Chem. Soc. 121 1999 6765 6766
115. T.M. Hallis, Z. Zhao, and H.-w. Liu J. Am. Chem. Soc. 122 2000 10493 10503
116. P.A. Frey Complex Pyridine Nucleotide-Dependent Transformations vol. 1 1987 John Wiley & Sons New York 462 510
117. A.J. Bauer, I. Rayment, P.A. Frey, and H.M. Holden Proteins 12 1992 372 381
118. J.R. Burke, and P.A. Frey Biochemistry 32 1993 13220 13230
119. J.B. Thoden, P.A. Frey, and H.M. Holden Biochemistry 35 1996 5137 5144
120. P.A. Frey FASEB 10 1996 461 470
121. H. Chen, Z. Guo, and H.-w. Liu J. Am. Chem. Soc. 120 1998 11796 11797
122. Z. Zhao, and H.-w. Liu J. Org. Chem. 66 2001 6810 6815
123. R.M. de Lederkremer, and W. Colli Glycobiology 5 1995 547 552
124. P.J. Brennan, and H. Nikaido Annu. Rev. Biochem. 64 1995 29 63
125. C. Whitfield Trends Microbiol. 3 1995 178 185
126. Q. Zhang, and H.-w. Liu J. Am. Chem. Soc. 123 2001 6756 6766
127. J.N. Barlow, M.E. Girvin, and J.S. Blanchard J. Am. Chem. Soc. 121 1999 6968 6969
128. Q. Zhang, and H.-w. Liu J. Am. Chem. Soc. 122 2000 9065 9070
129. Z. Huang, Q. Zhang, and H.-w. Liu Bioorganic Chem. 31 2003 494 502
130. M. Soltero-Higgin, E.E. Carlson, T.D. Gruber, and L.L. Kiessling Nat. Struct. Mol. Biol. 11 2004 539 543