Prioritization of charge over geometry in transition state analogues of a dual specificity protein kinase

Journal of the American Chemical Society

Volumn 133, Issue 11, 2011, Pages 3989-3994

  Xiaoxia, Liu ^a,b   Marston, James P ^a   Baxter, Nicola J ^a,c   Hounslow, Andrea M ^a   Yufen, Zhao ^b   Blackburn, G Michael ^a   Cliff, Matthew J ^a   Waltho, Jonathan P ^a,c  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b XIAMEN UNIVERSITY   (China)

^c UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE SITE; DIRECT OBSERVATION; FLUORINE ATOMS; ISOTOPE SHIFTS; MAGNESIUM IONS; MAP KINASE; METAL FLUORIDE; NMR ANALYSIS; PHOSPHORYL GROUPS; PRIORITIZATION; PROTEIN KINASE; PROTEIN RESIDUES; SIGNALING KINASE; TRANSITION-STATE ANALOGUES; TYROSINE PHOSPHORYLATION;

AMINO ACIDS; FLUORINE; FLUORINE COMPOUNDS; ISOTOPES; MAGNESIUM; METAL IONS; PHOSPHORYLATION;

ENZYMES;

ADENOSINE DIPHOSPHATE; CHEMICAL COMPOUND; FLUORINE; FLUOROALUMINATE; ISOTOPE; MAGNESIUM ION; MITOGEN ACTIVATED PROTEIN KINASE 14; MITOGEN ACTIVATED PROTEIN KINASE KINASE 6; PHENYLALANINE; PROTEIN KINASE; SOLVENT; TETRAFLUOROALUMINATE; TRANSITION STATE ANALOGUE; TYROSINE; UNCLASSIFIED DRUG;

ARTICLE; ATOM; BINDING SITE; CATALYSIS; ENZYME ACTIVE SITE; GEOMETRY; HUMAN; MUTATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN PHOSPHORYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; SURFACE CHARGE;

ALUMINUM COMPOUNDS; FLUORIDES; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PHOSPHORYLATION; PROTEIN CONFORMATION; PROTEIN KINASE INHIBITORS; PROTEIN KINASES; SUBSTRATE SPECIFICITY;

EID: 79952754518     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1090035     Document Type: Article

References (38)

1. Lad, C.; Williams, N. H.; Wolfenden, R. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 5607-5610
2. MEK 6; MAP/ERK Kinase6.
3. MAP mitogen activated protein kinase.
4. Bowler, M. W.; Cliff, M. J.; Waltho, J. P.; Blackburn, G. M. New J. Chem. 2010, 34, 784-794
5. Cleland, W. W.; Hengge, A. C. Chem. Rev. 2006, 106, 3252-3278
6. Wittinghofer, A. Curr. Biol. 1997, 7, R682-R685
7. Graham, D. L.; Lowe, P. N.; Grime, G. W.; Marsh, M.; Rittinger, K.; Smerdon, S. J.; Gamblin, S. J.; Eccleston, J. F. Chem. Biol. 2002, 9, 375-381
8. Messmore, J.; Raines, R. J. Am. Chem. Soc. 2000, 122, 9911-9916
9. Baxter, N. J.; Olguin, L. F.; Golicnik, M.; Feng, G.; Hounslow, A. M.; Bermel, W.; Blackburn, G. M.; Hollfelder, F.; Waltho, J. P.; Williams, N. H. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 14732-14727
10. Baxter, N. J.; Blackburn, G. M.; Marston, J. P.; Hounslow, A. M.; Cliff, M. J.; Bermel, W.; Williams, N. H.; Hollfelder, F.; Wemmer, D. E.; Waltho, J. P. J. Am. Chem. Soc. 2008, 130, 3952-3958
11. Baxter, N. J.; Hounslow, A. M.; Bowler, M. W.; Williams, N. H.; Blackburn, G. M.; Waltho, J. P. J. Am. Chem. Soc. 2009, 131, 16334-16335
12. Baxter, N. J.; Bowler, M. W.; Alizadeh, T.; Cliff, M. J.; Hounslow, A. M.; Wu, B.; Berkowitz, D. B.; Williams, N. H.; Blackburn, G. M.; Waltho, J. P. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 4555-4560
13. Cliff, M. J.; Bowler, M. W.; Varga, A.; Marston, J. P.; Szabo, J.; Hounslow, A. M.; Baxter, N. J.; Blackburn, G. M.; Vas, M.; Waltho, J. P. J. Am. Chem. Soc. 2010, 132, 6507-6516
14. Lee, J. Y.; Yang, W. Cell 2006, 127, 1349-1360
15. Huse, M.; Kuriyan, J. Cell 2002, 109, 275-282
16. Manning, G.; Whyte, D. B.; Martinez, R.; Hunter, T.; Sudarsanam, S. Science 2002, 298, 1912-1934
17. Pawson, T.; Scott, J. D. Trends Biochem. Sci. 2005, 30, 286-290
18. Fischer, E. H.; Krebs, E. G. J. Biol. Chem. 1955, 216, 121-132
19. Hunter, T. Curr. Opin. Cell Biol. 2009, 21, 140-146
20. Raingeaud, J.; Gupta, S.; Rogers, J. S.; Dickens, M.; Han, J.; Ulevitch, R. J.; Davis, R. J. J. Biol. Chem. 1995, 270, 7420-7426
21. Madhusudan; Akamine, P.; Xuong, N. H.; Taylor, S. S. Nat. Struct. Biol. 2002, 9, 273-277
22. Han, J.; Lee, J.; Jiang, Y.; Li, Z.; Feng, L.; Ulevitch, R. J. Biol. Chem. 1996, 271, 2886-2891
23. Raingeaud, J.; Whitmarsh, A. J.; Barrett, T.; Derijard, B.; Davis, R. J. Mol. Cell. Biol. 1996, 16, 1247-1255
24. Zhang, Y. Y.; Mei, Z. Q.; Wu, J. W.; Wang, Z. X. J. Biol. Chem. 2008, 283, 26591-601
25. Alonso, G.; Ambrosino, C.; Jones, M.; Nebreda, A. R. J. Biol. Chem. 2000, 275, 40641-40648
26. Golicnik, M.; Olguin, L. F.; Feng, G.; Baxter, N. J.; Waltho, J. P.; Williams, N. H.; Hollfelder, F. J. Am. Chem. Soc. 2009, 131, 1575-88
27. Anderson, K.; Murphy, A. J. Biol. Chem. 1983, 258, 14276-14278
28. Kinoshita, E.; Kinoshita-Kikuta, E.; Takiyama, K.; Koike, T. Mol. Cell. Proteomics 2006, 5, 749-757
29. Ferrell, J. E.; Bhatt, R. R. J. Biol. Chem. 1997, 272, 19008-19016
30. Askari, N.; Beenstock, J.; Livnah, O.; Engelberg, D. Biochemistry 2009, 48, 2497-2504
31. Turjanski, A. G.; Hummer, G.; Gutkind, J. S. J. Am. Chem. Soc. 2009, 131, 6141-6148
32. Hagen, D. S.; Weiner, J. H.; Sykes, B. D. Biochemistry 1979, 18, 2007-2012
33. Arnold, K.; Bordoli, L.; Kopp, J.; Schwede, T. Bioinformatics 2006, 22, 195-201
34. Jorgensen, W. L.; Maxwell, D. S.; Tirado-Rives, J. J. Am. Chem. Soc. 1996, 118, 11225-11236
35. Jorgensen, W. L.; Chandrasekhar, J.; Madura, J. D.; Impey, R. W.; Klein, M. L. J. Chem. Phys. 1983, 79, 926-935
36. Hess, B.; Kutzner, C.; van der Spoel, D.; Lindahl, E. J. Chem. Theory Comput. 2008, 4, 435-447
37. Meagher, K. L.; Redman, L. T.; Carlson, H. A. J. Comput. Chem. 2003, 24, 1016-1025
38. Kleywegt, G.; Jones, T. Acta Crystallogr., Sect. D 1998, 54, 1119-1131