Crystal Structure and Mechanistic Implications of N 2-(2-Carboxyethyl)arginine Synthase, the First Enzyme in the Clavulanic Acid Biosynthesis Pathway

Journal of Biological Chemistry

Volumn 279, Issue 7, 2004, Pages 5685-5692

  Caines, Matthew E C ^a   Elkins, Jonathan M ^a   Hewitson, Kirsty S ^a   Schofield, Christopher J ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BIOSYNTHESIS; CHROMATOGRAPHY; CONDENSATION; CRYSTAL STRUCTURE; ENZYMES; MASS SPECTROMETRY; METABOLITES;

GEL FILTRATION CHROMATOGRAPHY;

BIOCHEMISTRY;

AMINOPYRIDINE; ANION; ARGININE; BETA AMINO ACID; BETA LACTAMASE INHIBITOR; CLAVULANIC ACID; COCARBOXYLASE; DIMER; GLYCERALDEHYDE 3 PHOSPHATE; MAGNESIUM ION; N2 (2 CARBOXYETHYL)ARGININE SYNTHASE; SYNTHETASE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; BIOSYNTHESIS; CATALYSIS; CHEMICAL BOND; CRYSTAL STRUCTURE; ENZYME ACTIVE SITE; ENZYME CONFORMATION; ENZYME MECHANISM; GEL FILTRATION CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; POLYMERIZATION; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

AMINO ACIDS; ARGININOSUCCINATE LYASE; ARGININOSUCCINATE SYNTHASE; BINDING SITES; CHROMATOGRAPHY, GEL; CLAVULANIC ACID; CRYSTALLOGRAPHY, X-RAY; DIMERIZATION; MAGNESIUM; MASS SPECTROMETRY; MODELS, CHEMICAL; MODELS, MOLECULAR; MULTIENZYME COMPLEXES; STREPTOMYCES;

EID: 1242317003     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.M310803200     Document Type: Article

References (53)

1. Matagne, A., Dubus, A., Galleni, M., and Frère, J.-M. (1999) Nat. Prod. Rep. 16, 1-18
2. Jensen, S. E., and Paradkar, A. S. (1999) Antonie Leeuwenhoek Int. J. Gen. Mol. Microbiol. 75, 125-133
3. Baggaley, K. H., Brown, A. G., and Schofield, C. J. (1997) Nat. Prod. Rep. 14, 309-333
4. Brown, R. P., Aplin, R. T., and Schofield, C. J. (1996) Biochemistry 35, 12421-12432
5. Knowles, J. R. (1985) Acc. Chem. Res. 18, 97-104
6. Bentley, P. H., Brooks, G., Gilpin, M. L., and Hunt, E. (1979) Tetrahedron Lett. 20, 1889-1890
7. Mellado, E., Lorenzana, L. M., Rodriguez-Saiz, M., Diez, B., Liras, P., and Barredo, J. L. (2002) Microbiol. SGM 148, 1427-1438
8. Li, R. F., Khaleeli, N., and Townsend, C. A. (2000) J. Bacteriol. 182, 4087-4095
9. Hodgson, J. E., Fosberry, A. P., Rawlinson, N. S., Ross, H. N., Neal, R. J., Arnell, J. C., Earl, A. J., and Lawlor, E. J. (1995) Gene (Amst.) 166, 49-55
10. Jensen, S. E., Alexander, D. C., Paradkar, A. S., and Aidoo, K. A. (1993) in Industrial Microorganisms: Basic and Applied Molecular Genetics (Baltz, R. H., Hegeman, G. D., and Skatrud, P. L., eds) pp. 169-176, American Society for Microbiology, Washington, DC
11. Kershaw, N. J., McNaughton, H. J., Hewitson, K. S., Hernandez, H., Griffin, J., Hughes, C., Greaves, P., Barton, B., Robinson, C. V., and Schofield, C. J. (2002) Eur. J. Biochem. 269, 2052-2059
12. Khaleeli, N., Li, R., and Townsend, C. A. (1999) J. Am. Chem. Soc. 121, 9223-9224
13. McNaughton, H. J., Thirkettle, J. E., Zhang, Z., Schofield, C. J., and Jensen, S. E. (1998) J. Chem. Soc. Chem. Commun. 21, 2325-2326
14. Bachmann, B. O., Li, R., and Townsend, C. A. (1998) Proc. Natl. Acad. Sci. U. S. A. 95, 9082-9086
15. Nicholson, N. H., Baggaley, K. H., Cassels, R., Davison, M., Elson, S. W., Fulston, M., Tyler, J. W., and Woroniecki, S. R. (1994) J. Chem. Soc. Chem. Commun. 11, 1281-1282
16. Baldwin, J. E., Adlington, R. M., Bryans, J. S., Bringhen, A. O., Coates, J. B., Crouch, N. P., Lloyd, M. D., Schofield, C. J., Elson, S. W., Baggaley, K. H., Cassels, R., and Nicholson, N. (1991) Tetrahedron 47, 4089-4100
17. Wu, T.-K., Busby, R. W., Houston, T. A., McIlwaine, D. B., Egan, L. A., and Townsend, C. A. (1995) J. Bacteriol. 177, 3714-3720
18. Elson, S. W., Baggaley, K. H., Davidson, M., Fulston, M., Nicholson, N. H., and Risbridger, G. D. (1993) J. Chem. Soc. Chem. Commun. 15, 1212-1214
19. Aidoo, K. A., Wong, A., Alexander, D. C., Rittamer, R. A., and Jensen, S. (1994) Gene (Amst.) 147, 41-46
20. Miller, M. T., Bachmann, B. O., Townsend, C. A., and Rosenzweig, A. C. (2001) Nat. Struct. Biol. 8, 684-689
21. Elkins, J. M., Clifton, I. J., Hernandez, H., Doan, L. X., Robinson, C. V., Schofield, C. J., and Hewitson, K. S. (2002) Biochem. J. 366, 423-434
22. Zhang, Z., Ren, J., Stammers, D. K., Baldwin, J. E., Harlos, K., and Schofield, C. J. (2000) Nat. Struct. Biol. 7, 127-133
23. Jordan, F. (2003) Nat. Prod. Rep. 20, 184-201
24. Hasson, M. S., Muscate, A., McLeish, M. J., Polovnikova, L. S., Gerlt, J. A., Kenyon, G. L., Petsko, G. A., and Ringe, D. (1998) Biochemistry 37, 9918-9930
25. Muller, Y. A., and Schulz, G. E. (1993) Science 259, 965-967
26. Bertagnolli, B. L., and Hager, L. P. (1991) J. Biol. Chem. 266, 10168-10173
27. Foulon, V., Antonenkov, V. D., Croes, K., Waelkens, E., Mannaerts, G. P., Van Veldhoven, P. P., and Casteels, M. (1999) Proc. Natl. Acad. Sci. U. S. A. 96, 10039-10044
28. Leslie, A. G. (1999) Acta Crystallogr. Sect. D Biol. Crystallogr. 55, 1696-1702
29. Collaborative Computational Project Number 4 (1994) Acta Crystallogr. Sect. D Biol. Crystallogr. 50, 760-763
30. Schneider, T. R., and Sheldrick, G. M. (2002) Acta Crystallogr. Sect. D Biol. Crystallogr. 54, 1772-1779
31. Brunger, A. T., Adams, P. D., Clore, G. M., DeLano, W. L., Gros, P., Grosse-Kunstleve, R. W., Jiang, J. S., Kuszewski, J., Nilges, M., Pannu, N. S., Read, R. J., Rice, L. M., Simonson, T., and Warren, G. L. (1998) Acta Crystallogr. Sect. D Biol. Crystallogr. 54, 905-921
32. Jones, T. A., Zou, J. Y., Cowan, S. W., and Kjeldgaard, M. (1991) Acta Crystallogr. Sect. A 47, 110-119
33. Murshudov, G. N., Vagin, A. A., Lebedev, A., Wilson, K. S., and Dodson, E. J. (1999) Acta Crystallogr Sect. D Biol. Crystallogr. 55, 247-255
34. Laskowski, R. A., MacArthur, M. W., Moss, D. S., and Thornton, J. M. (1993) J. Appl. Crystallogr. 26, 283-291
35. Kraulis, P. J. (1991) J. Appl. Crystallogr. 24, 946-950
36. Esnouf, R. M. (1997) J. Mol. Graph. Model. 15, 132-134
37. Merritt, E. A., and Bacon, D. J. (1997) Methods Enzymol. 277, 505-524
38. Arjunan, P., Umland, T., Dyda, F., Swaminathan, S., Furey, W., Sax, M., Farrenkopf, B., Gao, Y., Zhang, D., and Jordan, F. (1996) J. Mol. Biol. 256, 590-600
39. Lu, G. G., Dobritzsch, D., Baumann, S., Schneider, G., and König, S. (2000) Eur. J. Biochem. 267, 861-868
40. Dobritzsch, D., König, S., Schneider, G., and Lu, G. (1998) J. Biol. Chem. 273, 20196-20204
41. Hawkins, C. F., Borges, A., and Perham, R. N. (1989) FEBS Lett. 255, 77-82
42. Guo, F. S., Zhang, D. Q., Kahyaoglu, A., Farid, R. S., and Jordan, F. (1998) Biochemistry 37, 13379-13391
43. Nilsson, U., Meshalkina, L., Lindqvist, Y., and Schneider, G. (1997) J. Biol. Chem. 272, 1864-1869
44. Pang, S. S., Duggleby, R. G., and Guddat, L. W. (2002) J. Mol. Biol. 317, 249-262
45. McIlwaine, D. B., and Townsend, C. A. (1993) J. Chem. Soc. Chem. Commun. 17, 1346-1347
46. Basak, A., Salowe, S. P., and Townsend, C. A. (1990) J. Am. Chem. Soc. 112, 1654-1656
47. Kern, D., Kern, G., Neef, H., Tittmann, K., Killenberg-Jabs, M., Wikner, C., Schneider, G., and Hubner, G. (1997) Science 275, 67-70
48. Schellenberger, A. (1998) Biochim. Biophys. Acta Protein Struct. 1385, 177-186
49. Schellenberger, A. (1990) Chem. Ber. 123, 1489-1494
50. Golbik, R., Neef, H., Hubner, G., König, S., Seliger, B., Meshalkina, L., Kochetov, G. A., and Schellenberger, A. (1991) Bioorg. Chem. 19, 10-17
51. Fiedler, E., Thorell, S., Sandalova, T., Golbik, R., König, S., and Schneider, G. (2002) Proc. Natl. Acad. Sci. U. S. A. 99, 591-595
52. Lobell, M., and Crout, D. H. G. (1996) J. Am. Chem. Soc. 118, 1867-1873
53. Polovnikova, E. S., McLeish, M. J., Sergienko, E. A., Burgner, J. T., Anderson, N. L., Bera, A. K., Jordan, F., Kenyon, G. L., and Hasson, M. S. (2003) Biochemistry 42, 1820-1830