Enolpyruvyl activation by enolpyruvylshikimate-3-phosphate synthase

Biochemistry

Volumn 46, Issue 7, 2007, Pages 1933-1940

  Clark, Meghann E ^b   Berti, Paul J ^a,b  

^a MCMASTER UNIVERSITY   (Canada)

^b MCMASTER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ENOLPYRUVYL REACTIONS; NUCLEOPHILIC ADDITION; PHOSPHOENOLPYRUVATE;

ADDITION REACTIONS; AMINO ACIDS; BIOSYNTHESIS; CATALYSIS; DISSOCIATION; HYDROLYSIS;

ENZYME KINETICS;

AROMATIC AMINO ACID; ENOYLPYRUVYLSHIKIMATE 3 PHOSPHATE SYNTHASE; ENZYME INHIBITOR; PHOSPHOENOLPYRUVATE; POTASSIUM HYDROXIDE; PYRUVIC ACID; SHIKIMIC ACID; TRANSFERASE; UNCLASSIFIED DRUG;

AMINO ACID SYNTHESIS; AQUEOUS SOLUTION; ARTICLE; CATALYSIS; DISSOCIATION; ENZYME ACTIVE SITE; HYDROLYSIS; NONHUMAN; PRIORITY JOURNAL; PROTON TRANSPORT; REACTION ANALYSIS;

3-PHOSPHOSHIKIMATE 1-CARBOXYVINYLTRANSFERASE; BINDING SITES; CATALYSIS; CATIONS, MONOVALENT; ENZYME ACTIVATION; HYDROLYSIS; HYDROXIDES; KINETICS; MODELS, MOLECULAR; POTASSIUM COMPOUNDS; SHIKIMIC ACID; SOLUTIONS; WATER;

EID: 33847043159     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi0618316     Document Type: Article

References (50)

1. Anderson, K. S., and Johnson, K. A. (1990) Kinetic and structural analysis of enzyme intermediates: Lessons from EPSP synthase, Chem. Rev. 90, 1131-1149.
2. Roberts, F., Roberts, C. W., Johnson, J. J., Kyle, D. E., Krell, T., Coggins, J. R., Coombs, G. H., Milhous, W. K., Tzipori, S., Ferguson, D. J., Chakrabarti, D., and McLeod, R. (1998) Evidence for the shikimate pathway in apicomplexan parasites, Nature 393, 801-805.
3. Steinrucken, H. C., and Amrhein, N. (1980) The herbicide glyphosate is a potent inhibitor of 5-enolpyruvyl-shikimic acid-3-phosphate synthase, Biochem. Biophys. Res. Commun. 94, 1207-1212.
4. Kahan, F. M., Kahan, J. S., Cassidy, P. J., and Kropp, H. (1974) Mechanism of action of fosfomycin (phosphonomycin), Ann. N. Y. Acad. Sci. 235, 364-386.
5. Mizyed, S., Wright, J. E. I., Byczynski, B., and Berti, P. J. (2003) Identification of the catalytic residues of AroA (enolpyruvylshikimate 3-phosphate synthase) using partitioning analysis, Biochemistry 42, 6986-6995.
6. Eschenburg, S., Kabsch, W., Healy, M. L., and Schonbrunn, E. (2003) A new view of the mechanisms of UDP-N-acetylglucosamine enolpyruvyl transferase (MurA) and 5-enolpyruvylshikimate-3-phosphate synthase (AroA) derived from x-ray structures of their tetrahedral reaction intermediate states, J. Biol. Chem. 278, 49215-49222.
7. An, M., Maitra, U., Neidlein, U., and Bartlett, P. A. (2003) 5-Enolpyruvylshikimate 3-phosphate synthase: Chemical synthesis of the tetrahedral intermediate and assignment of the stereochemical course of the enzymatic reaction, J. Am. Chem. Sac. 125, 12759-12767.
8. Anton, D. L., Hedstrom, L., Fish, S., and Abeles, R. H. (1983) Mechanism of enolpyruvylshikimate-3-phosphate synthase exchange of phosphoenolpyruvate with solvent protons, Biochemistry 22, 5903-5908.
9. Steinrucken, H. C., and Amrhein, N. (1984) 5-Enolpyruvylshikimate-3- phosphate synthase of Klebsiella pneumoniae 2. Inhibition by glyphosate [N-(phosphonomethyl)glycine], Eur. J. Biochem. 143, 351-357.
10. Boocock, M. R., and Coggins, J. R. (1983) Kinetics of 5-enolpyravylshikimate-3-phosphate synthase inhibition by glyphosate, FEBS Lett. 154, 127-133.
11. Sammons, R. D., Grays, K. J., Anderson, K. S., Johnson, K. A., and Sikorski, J. A. (1995) Reevaluating glyphosate as a transition-state inhibitor of EPSP synthase: identification of an EPSP synthase·EPSP· glyphosate ternary complex, Biochemistry 34, 6433-6440.
12. Leo, G. C., Sikorski, J. A., and Sammons, R. D. (1990) Novel product from EPSP synthase at equilibrium, J. Am. Chem. Soc. 112, 1653-1654.
13. 13C NMR of the EPSP synthase tetrahedral intermediate bound to the enzyme active site, Biochemistry 29, 1460-1465.
14. 13C NMR spectroscopy, Biochemistry 28, 7985-7991 [erratum: (1989) Biochemistry 28, 10093].
15. Studelska, D. R., McDowell, L. M., Espe, M. P., Klug, C. A., and Schaefer, J. (1997) Slowed enzymatic turnover allows characterization of intermediates by solid-state NMR, Biochemistry 36, 15555-15560.
16. Byczynski, B., Mizyed, S., and Berti, P. J. (2003) Nonenzymatic breakdown of the tetrahedral (α-carboxyketal phosphate) intermediates of MurA and AroA, two carboxyvinyl transferases. Protonation of different functional groups controls the rate and fate of breakdown, J. Am. Chem. Soc. 125, 12541-12550.
17. Kresge, A. J., Sagatys, D. S., and Chen, H. L. (1977) Vinyl ether hydrolysis. 9. Isotope effects on proton-transfer from hydronium ion, J. Am. Chem. Soc. 99, 7228-7233.
18. Kirby, A. J., and Williams, N. H. (1991) Efficient intramolecular general acid catalysis of vinyl ether hydrolysis by the neighboring carboxylic acid group, J. Chem. Soc., Chem. Commun., 1643-1644.
19. Kirby, A. J., and Williams, N. H. (1991) There is no evidence for electrostatic catalysis of vinyl ether hydrolysis in water, J. Chem. Soc., Chem. Commun., 1644-1645.
20. Loudon, G. M., Smith, C. K., and Zimmerman, S. E. (1974) Concurrent general acid-electrostatic catalysis in vinyl ether hydrolysis and aspartic-52 of lysozyme, J. Am. Chem. Soc. 96, 465-479.
21. Kresge, A. J. (1987) Unusual reactivity of prostacyclin-rational drag design through physical organic-chemistry, Ace. Chem. Res. 20, 364-370.
22. Kresge, A. J., Leibovitch, M., and Sikorski, J. A. (1992) Acid-catalyzed hydrolysis of 5-enolpyruvylshikimate 3-phosphate (EPSP) and some simple models of its vinyl ether functional group, J. Am. Chem. Soc. 114, 2618-2622.
23. Anderson, K. S., Sikorski, J. A., and Johnson, K. A. (1988) Evaluation of 5-enolpyruvoylshikimate-3-phosphate synthase substrate and inhibitor binding by stopped-flow and equilibrium fluorescence measurements, Biochemistry 27, 1604-1610.
24. Duggleby, R. G. (1983) Determination of the kinetic properties of enzymes catalysing coupled reaction sequences, Biochim. Biophys. Acta 744, 249-259.
25. Zhang, F., and Berti, P. J. (2006) Phosphate analogues as probes of the catalytic mechanisms of MurA and AroA, two carboxyvinyl transferases, Biochemistry 45, 6027-6037.
26. Anderson, K. S., Sikorski, J. A., and Johnson, K. A. (1988) A tetrahedral intermediate in the EPSP synthase reaction observed by rapid quench kinetics, Biochemistry 27, 7395-7406.
27. Anderson, K. S., and Johnson, K. A. (1990) "Kinetic competence" of the 5-enolpyruvoylshikimate-3-phosphate synthase tetrahedral intermediate, J. Biol. Chem. 265, 5567-5572.
28. Gruys, K. J., Walker, M. C., and Sikorski, J. A. (1992) Substrate synergism and the steady-state kinetic reaction mechanism for EPSP synthase from Escherichia coli, Biochemistry 31, 5534-5544.
29. Grays, K. J., Marzabadi, M. R., Pansegrau, P. D., and Sikorski, J. A. (1993) Steady-state kinetic evaluation of the reverse reaction for Escherichia coli 5-enolpyruvoylshikimate-3-phosphate synthase, Arch. Biochem. Biophys. 304, 345-351.
30. Barshop, B. A., Wrenn, R. F., and Frieden, C. (1983) Analysis of numerical methods for computer simulation of kinetic processes: development of KINSIM-a flexible, portable system, Anal. Biochem. 130, 134-145.
31. Zimmerle, C. T., and Frieden, C. (1989) Analysis of progress curves by simulations generated by numerical integration, Biochem. J. 258, 381-387.
32. Cox, R. A., and Yates, K. (1978) Excess acidities-generalized method for determination of basicities in aqueous acid mixtures, J. Am. Chem. Soc. 100, 3861-3867.
33. Belarmino, A. T. N., Froehner, S., Zanette, D., Farah, J. P. S., Bunton, C. A., and Romsted, L. S. (2003) Effect of alkyl group size on the mechanism of acid hydrolyses of benzaldehyde acetals, J. Org. Chem. 68, 706-717.
34. Wiberg, K. B., and Squires, R. R. (1981) Thermochemical studies of carbonyl reactions. 2. Steric effects in acetal and ketal hydrolysis, J. Am. Chem. Soc. 103, 4473-4478.
35. Cleland, W. W. (1990) Kinetic competence of enzymic intermediates: fact or fiction?, Biochemistry 29, 3194-3197.
36. Charton, M. (1964) Definition of "inductive" substituent constants, J. Org. Chem. 29, 1222-1227.
37. a values. Oxalic and squaric acids, Anal. Chem. 43, 1110-1113.
38. Pinching, G. D., and Bates, R. G. (1948) Second dissociation constant of oxalic acid from 0° to 50° and the pH of certain oxalate buffer solutions, J. Res. Natl. Bur. Stand. 40, 405-416 (research paper no. 1885).
39. Ritchie, C. D. (1975) Cation-anion combination reactions. XIII. Correlation of the reactions of nucleophiles with esters, J. Am. Chem. Soc. 97, 1170-1179.
40. Schonbrunn, E., Eschenburg, S., Shuttleworth, W. E., Schloss, J. V., Amrhein, N., Evans, J. N. S., and Kabsch, W. (2001) Interaction of the herbicide glyphosate with its target enzyme 5-enolpyruvylshikimate 3-phosphate synthase in atomic detail, Proc. Natl. Acad. Sci. U.S.A. 98, 1376-1380.
41. Sinnott, M. L. (1990) Catalytic mechanisms of enzymic glycosyl transfer, Chem. Rev. 90, 1171-1202.
42. Zechel, D. L., and Withers, S. G. (2000) Glycosidase mechanisms: Anatomy of a finely tuned catalyst, Ace. Chem. Res. 33, 11-18.
43. Berti, P. J., and Tanaka, K. S. E. (2002) Transition state analysis using multiple kinetic isotope effects: Mechanisms of enzymatic and non-enzymatic glycoside hydrolysis and transfer, Adv. Phys. Org. Chem. 57, 239-314.
44. Richard, J. P., Williams, K. B., and Amyes, T. L. (1999) Intrinsic barriers for the reactions of an oxocarbenium ion in water, J. Am. Chem. Soc. 121, 8403-8404.
45. Richard, J. P. (1995) A consideration of the barrier for carbocation-nucleophile combination reactions, Tetrahedron 51, 1535-1573.
46. Knoll, T. L., and Bennet, A. J. (2004) Aqueous methanolysis of an alpha-D-N-acetylneuraminyl pyridinium zwitterion: solvolysis occurs with no intramolecular participation of the anomeric carboxylate group, J. Phys. Org. Chem. 17, 478-482.
47. Horenstein, B. A., and Bruner, M. (1998) The N-acetyl neuraminyl oxocarbenium ion is an intermediate in the presence of anionic nucleophiles, J. Am. Chem. Soc. 120, 1357-1362.
48. 14C isotope effect, J. Am. Chem. Soc. 119, 1101-1107.
49. Bols, M. (1998) 1-Aza sugars, apparent transition state analogues of equatorial glycoside formation/cleavage, Ace. Chem. Res. 31, 1-8.
50. Lillelund, V. H., Jensen, H. H., Liang, X., and Bols, M. (2002) Recent developments of transition-state analogue glycosidase inhibitors of non-natural product origin, Chem. Rev. 102, 515-553.