Structural, functional and calorimetric investigation of MosA, a dihydrodipicolinate synthase from Sinorhizobium meliloti L5-30, does not support involvement in rhizopine biosynthesis

ChemBioChem

Volumn 9, Issue 10, 2008, Pages 1591-1602

  Phenix, Christopher P ^a,b   Nienaber, Kurt ^a   Tam, Pui Hang ^a,c   Delbaere, Louis T J ^a   Palmer, David R J ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

^b TRIUMF   (Canada)

^c UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Inhibitors; Isothermal titration microcalorimetry; Rhizopine; Schift bases; Synthases

Indexed keywords

2 OXOBUTYRIC ACID; AMINOCYCLITOL; BACTERIAL ENZYME; BACTERIAL PROTEIN; DIHYDRODIPICOLINATE SYNTHASE; METHYLTRANSFERASE; PROTEIN MOSA; PYRUVIC ACID; S ADENOSYLMETHIONINE; SCHIFF BASE; SCYALLOINOSAMINE; SODIUM BOROHYDRIDE; UNCLASSIFIED DRUG; DRUG DERIVATIVE; INOSITOL; LYASE; MOSA PROTEIN, RHIZOBIUM MELILOTI; RHIZOPINE;

ARTICLE; BIOSYNTHESIS; COMPETITIVE INHIBITION; CONTROLLED STUDY; CRYSTAL STRUCTURE; ENZYME STRUCTURE; ISOTHERMAL TITRATION CALORIMETRY; NONHUMAN; PRIORITY JOURNAL; PROTEIN FUNCTION; PROTEIN INTERACTION; SEQUENCE HOMOLOGY; SINORHIZOBIUM MELILOTI; THERMODYNAMICS; CALORIMETRY; CHEMICAL STRUCTURE; CHEMISTRY; CRYSTALLOGRAPHY; ENZYME SPECIFICITY; ENZYMOLOGY; KINETICS; MACROMOLECULE; METABOLISM; MICROBIOLOGY;

BACTERIA (MICROORGANISMS); FABACEAE; SINORHIZOBIUM MELILOTI;

BACTERIAL PROTEINS; CALORIMETRY; CARBON-CARBON LYASES; CRYSTALLOGRAPHY; INOSITOL; KINETICS; MACROMOLECULAR SUBSTANCES; MODELS, MOLECULAR; S-ADENOSYLMETHIONINE; SINORHIZOBIUM MELILOTI; SOIL MICROBIOLOGY; SUBSTRATE SPECIFICITY;

EID: 48249086676     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200700569     Document Type: Article

References (51)

1. E. M. Lodwig, A. H. F. Hosie, A. Bordes, K. Findlay, D. Allaway, R. Karunakaran, J. A. Downie, P. S. Poole, Nature 2003, 422, 722-726.
2. J. Sprent, New Phytol. 2007, 174, 11-25.
3. P. J. Murphy, W. Wexler, W. Grzemski, J. P. Rao, D. Gordon, Soil Biol. Biochem. 1995, 27, 525-529.
4. P. J. Murphy, N. Heycke, S. P. Trenz, P. Ratet, F. J. Debruijn, J. Schell, Proc. Natl. Acad Sci. USA 1988, 85, 9133-9137.
5. P. J. Murphy, S. P. Trenz, W. Grzemski, F. J. Debruijn, J. Schell, J. Bacteriol. 1993, 175, 5193-5204.
6. P. J. Murphy, N. Heycke, Z. Banfalvi, M. E. Tate, F. Debruijn, A. Kondorosi, J. Tempe, J. Schell, Proc. Natl. Acad. Sci. USA 1987, 84, 493-497.
7. M. C. Lawrence, J. A. R. G. Barbosa, B. J. Smith, N. E. Hall, P. A. Pilling, H. C. Ooi, S. M. Marcuccio, J. Mol. Biol. 1997, 266, 381-399.
8. P. C. Babbitt, J. A. Gerlt, J. Biol. Chem. 1997, 272, 30591-30594.
9. S. Blickling, C. Renner, B. Laber, H. D. Pohlenz, T. A. Holak, R. Huber, Biochemistry 1997, 36, 24-33.
10. G. Scapin, J. S. Blanchard, Advances in Enzymology, Vol. 72 1998, p. 279.
11. R. C. J. Dobson, S. R. A. Devenish, L. A. Turner, V. R. Clifford, F. G. Pearce, G. B. Jameson, J. A. Gerrard, Biochemistry 2005, 44, 13007-13013.
12. R. C. J. Dobson, J. A. Gerrard, F. G. Pearce, Biochem. J. 2004, 377, 757-762.
13. R. C. J. Dobson, M. D. W. Griffin, G. B. Jameson, J. A. Gerrard, Acta Crystallogr. Sect. D Biol. Crystallogr. 2005, 61, 1116-1124.
14. R. C. J. Dobson, M. D. W. Griffin, S. J. Roberts, J. A. Gerrard, Biochimie 2004, 86, 311-315.
15. R. C. J. Dobson, K. Valegard, J. A. Gerrard, J. Mol. Biol. 2004, 338, 329-339.
16. J. J. Turner, J. A. Gerrard, C. A. Hutton, Bioorg. Med. Chem. 2005, 13, 2133-2140.
17. J. J. Turner, J. P. Healy, R. C. J. Dobson, J. A. Gerrard, C. A. Hutton, Bioorg. Med. Chem. Lett. 2005, 15, 995-998.
18. P. H. Tam, C. P. Phenix, D. R. J. Palmer, J. Mol. Biol. 2004, 335, 393-397.
19. P. Lestrate, A. Dricot, R. M. Delrue, C. Lambert, V. Martinelli, X. De Bolle, J. J. Letesson, A. Tibor, Infect. Immun. 2003, 71, 7053-7060.
20. C. P. Saint, M. Wexler, P. J. Murphy, J. Tempe, M. E. Tate, P. J. Murphy, J. Bacteriol. 1993, 175, 5205-5215.
21. P. M. Flatt, T. Mahmud, Nat. Prod. Rep. 2007, 24, 358-392.
22. T. J. Donohoe, P. D. Johnson, R. J. Pye, M. Keenan, Org. Lett. 2005, 7, 1275-1277.
23. P. Serrano, J. Casas, M. Zucco, G. Emeric, M. Egido-Gabas, A. Llebaria, A. Delgado, J. Comb. Chem. 2007, 9, 43-52.
24. L. Anderson, H. A. Lardy, J. Am. Chem. Soc. 1950, 72, 3141-3147.
25. G. I. Drummond, J. N. Aronson, L. Anderson, J. Org. Chem. 1961, 26, 1601-1607.
26. T. Suami, F.W. Lichtenthaler, S. Ogawa, Bull. Chem. Soc. Jpn. 1966, 39, 170-178.
27. M. Egido-Gabás, P. Serrano, J. Casas, A. Llebaria, A. Delgado, Org. Biomol. Chem. 2005, 3, 1195-1201.
28. J. B. Walker, M. S. Walker, Biochemistry 1967, 6, 3821-3829.
29. J. B. Walker, Appl. Environ. Microbiol. 2002, 68, 2404-2410.
30. A. Krief, W. Dumont, D. Billen, J. J. Letesson, P. Lestrate, P. J. Murphy, D. Lacroix, Tetrahedron Lett. 2004, 45, 1461-1463.
31. S. Koto, M. Hirooka, T. Yoshida, K. Takenaka, C. Asai, T. Nagamitsu, H. Sakuma, M. Sakurai, S. Masuzawa, M. Komiya, T. Sato, S. Zen, K. Yago, F Tomonaga, Bull. Chem. Soc. Jpn. 2000, 73, 2521-2529.
32. V. N. Azev, M. d'Alarcao, J. Org. Chem. 2004, 69, 4839-4842.
33. Collaborative Computational Project, Number 4, Acta Crystallogr. Sect. D Biol. Crystallogr. 1994, 50, 760-763.
34. R. A. Laskowski, M. W. Macarthur, D. S. Moss, J. M. Thornton, J. Appl. Crystallogr. 1993, 26, 283-291.
35. M. A. Perugini, M. D. W. Griffin, B. J. Smith, L. E. Webb, A. J. Davis, E. Handman, J. A. Gerrard, Eur. Biophys. J. 2005, 34, 469-476.
36. L. Holm, J. Park, Bioinformatics 2000, 16, 566-567.
37. R. J. Cox, Nat. Prod. Rep. 1996, 13, 29-43.
38. W. E. Karsten, Biochemistry 1997, 36, 1730-1739.
39. M. Dixon, Biochem. J. 1953, 55, 170-171.
40. B. Laber, F. X. Gomisruth, M. J. Romao, R. Huber, Biochem. J. 1992, 288, 691-695.
41. X. L. Zhu, J. B. Cai, J. Yang, Q. D. Su, Carbohydr. Res. 2005, 340, 1732-1738.
42. R. Talhout, A. Villa, A. E. Mark, J. B. F. N. Engberts, J. Am. Chem. Soc. 2003, 125, 10570-10579.
43. A. Velazquez-Campoy, E. Freire, Biophys. Chem. 2005, 775, 115, 115-124.
44. S. Leavitt, E. Freire, Curr. Opin. Struct. Biol. 2001, 11, 560-566.
45. W. B. Turnbull, A. H. Daranas, J. Am. Chem. Soc. 2003, 125, 14859-14866.
46. A. P. Brogan, W. R. Widger, D. Bensadek, I. Riba-Garcia, S. J. Gaskell, H. Kohn, J. Am. Chem. Soc. 2005, 127, 2741-2751.
47. S. J. Roberts, J. C. Morris, R. C. J. Dobson, C. L. Baxter, J. A. Gerrard, Arkivoc 2004, 166-177.
48. D. C. Billington, R. Baker, J. J. Kulagowski, I. M. Mawer, J. P. Vacca, S. J. Desolms, J. R. Huff, J. Chem. Soc. Perkin Trans. 1 1989, 1423-1429.
49. E. B. Borthwick, S. J. Connell, D. W. Tudor, D. J. Robins, A. Shneier, C. Abell, J. R. Coggins, Biochem. J. 1995, 305, 521-524.
50. Y. A. Leduc, C. P. Phenix, J. Puttick, K. Nienaber, D. R. J. Palmer, L. T. J. Delbaere, Acta Crystallogr. Sect. F Struct. Biol. Cryst. Commun. 2006, 62, 49-51.
51. A. Leslie in MOSFLM Users Guide, MRC Laboratory of Molecular Biology, Cambridge, 1995.