Dihydrodipicolinate synthase is not inhibited by its substrate, (S)-aspartate β-semialdehyde

Biochemical Journal

Volumn 377, Issue 3, 2004, Pages 757-762

  Dobson, Renwick C J ^a   Gerrard, Juliet A ^a   Pearce, F Grant ^a  

^a UNIVERSITY OF CANTERBURY   (New Zealand)

Author keywords

Aspartate semialdehyde; Dihydrodipicolinate synthase; Lysine biosynthesis; Substrate inhibition

Indexed keywords

BIOCHEMISTRY; BIOSYNTHESIS; CATALYSIS; ENZYME INHIBITION; ESCHERICHIA COLI; HERBICIDES; PLANTS (BOTANY);

ANTI-MICROBIAL ACTIONS;

ENZYMES;

ALDEHYDE DERIVATIVE; ASPARTATE BETA SEMIALDEHYDE; DIHYDRODIPICOLINATE SYNTHASE; PICOLINIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ELECTROSPRAY MASS SPECTROMETRY; LIQUID CHROMATOGRAPHY; OZONOLYSIS; PRIORITY JOURNAL; SYNTHESIS;

ESCHERICHIA COLI;

EID: 1242337331     PISSN: 02646021     EISSN: None     Source Type: Journal    
DOI: 10.1042/bj20031389     Document Type: Article

References (25)

1. Cox, R. J., Sutherland, A. and Vederas, J. C. (2000) Bacterial diaminopimelate metabolism as a target for antibiotic design. Bioorg. Med. Chem. Lett. 8, 843-871
2. Hutton, C. A., Southwood, T. J. and Turner, J. J. (2003) Inhibitors of lysine biosynthesis as antibacterial agents. Mini Rev. Med. Chem. 3, 115-127
3. Mazelis, M., Whatley, F. R. and Whatley, J. (1997) The enzymology of lysine biosynthesis in higher plants. FEBS Lett. 84, 236-240
4. Blickling, S., Renner, C., Laber, B., Pohlenz, H.-D., Holak, T. A. and Huber, R. (1997) Reaction mechanism of Escherichia coli dihydrodipicolinate synthase investigated by X-ray crystallography and NMR spectroscopy. Biochemistry 36, 24-33
5. Karsten, W. E. (1997) Dihydrodipicolinate synthase from Escherichia coli: pH dependent changes in the kinetic mechanism and kinetic mechanism of allosteric inhibition by L-lysine. Biochemistry 36, 1730-1739
6. Yugari, Y. and Gilvarg, C. (1965) The condensation step in diaminopimelate synthesis. J. Biol. Chem. 240, 4710-4716
7. Shedlarski, J. C. and Gilvarg, C. (1970) The pyruvate-aspartic semialdehyde condensing enzyme of Escherichia coli. J. Biol. Chem. 245, 1362-1373
8. Negrutiu, I., Cattoir-Reynearts, A., Verbruggen, I. and Jacobs, M. (1984) Lysine overproducer mutants with an altered dihydrodipicolinate synthase from protoplast culture of Nicotiana sylvestris. Theor. Appl. Genet. 68, 11-20
9. Kumpaisal, R., Hashimoto, T. and Yamada, Y. (1987) Purification and characterization of dihydrodipicolinate synthase from wheat suspension cultures. Plant Physiol. 85, 145-151
10. Ghislain, M., Frankard, V. and Jacobs, M. (1995) A dinucleotide mutation in dihydrodipicolinate synthase of Nicotiana sylvestris leads to lysine overproduction. Plant J. 8, 733-743
11. Frisch, D. A., Gengenbach, B. G., Tommey, A. M., Sellner, J. M., Somers, D. A. and Myers, D. E. (1991) Isolation and characterization of dihydrodipicolinate synthase from maize. Plant Physiol. 96, 444-452
12. Dereppe, C., Bold, G., Ghisalba, O., Ebert, E. and Schar, H.-P. (1992) Purification and characterization of dihydrodipicolinate synthase from pea. Plant Physiol. 98, 813-821
13. Borthwick, E. B., Connel, S. J., Tudor, D. W., Robins, D. J., Shneier, A., Abell, C. and Coggins, J. R. (1995) Escherichia coli dihydrodipicolinate synthase: characterisation of the imine intermediate and the product of bromopyruvate treatment by electrospray mass spectrometry. Biochem. J. 305, 521-524
14. Coulter, C. V., Gerrard, J. A., Kraunsoe, J. A. E. and Pratt, A. J. (1999) Escherichia coli dihydrodipicolinate synthase and dihydrodipicolinate reductase: kinetic and inhibition studies of two putative herbicide targets. Pestic. Sci. 55, 887-895
15. Laber, B., Gomis-Ruth, F. X., Romao, M. J. and Huber, R. (1992) Escherichia coli dihydrodipicolinate synthase. Identification of the active site and crystallization. Biochem. J. 288, 691-695
16. Cornish-Bowden, A. (1999) Fundamentals of Enzyme Kinetics, Portland Press, London
17. Stahly, D. P. (1969) Dihydrodipicolinate synthase of Bacillus licheniformis. Biochim. Biophys. Acta 191, 439-451
18. Wallsgrove, R. M. and Mazelis, M. (1981) Spinach leaf dihydrodipicolinate synthase: partial purification and characterization. Biochemistry 20, 2651-2655
19. Roberts, S. J., Morris, J. C., Dobson, R. C. J. and Gerrard, J. A. (2003) The preparation of (S)-aspartate semi-aldehyde appropriate for use in biochemical studies. Bioorg. Med. Chem. Lett. 13, 265-267
20. Bradford, M. M. (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of prutein-dye binding. Anal. Biochem. 72, 248-254
21. Coulter, C. V., Gerrard, J. A., Kraunsoe, J. A. E. and Pratt, A. J. (1996) (S)-Aspartate semi-aldehyde: synthetic and structural studies. Tetrahedron 52, 7127-7136
22. Black, S. and Wright, N. G. (1954) Aspartic β-semialdehyde dehydrogenase and aspartic β-semialdehyde. J. Biol. Chem, 213, 39-50
23. Kumpaisal, R., Hashimoto, T. and Yamada, Y. (1989) Inactivation of wheat dihydrodipicolinate synthase by 3-bromopyruvate. Agric. Biol. Chem. 53, 355-359
24. Tudor, D. W., Lewis, T. and Robbins, D. J. (1993) Synthesis of the trifluoroacetate salt of aspartic acid β-semialdehyde, an intermediate in the biosynthesis of L-lysine, L-threonine, and L-methionine. Synthesis 11, 1061-1062
25. March, J. (1992) Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, Wiley, New York