Synthesis and characterization of intermediate and transition-state analogue inhibitors of γ-glutamyl peptide ligases

Bioscience, Biotechnology and Biochemistry

Volumn 63, Issue 12, 1999, Pages 2248-2251

  Inoue, Makoto ^a   Hiratake, Jun ^a   Sakata, Kanzo ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Intermediate analogue; Phosphonodifluoromethyl ketone; Phosphonofluoridate; Transition state analogue; glutamyl peptide ligase

Indexed keywords

ADENOSINE TRIPHOSPHATE; ENZYME INHIBITOR; GLUTAMATE AMMONIA LIGASE; GLUTAMATE CYSTEINE LIGASE;

ARTICLE; CHEMICAL MODEL; DRUG ANTAGONISM; ENZYMOLOGY; ESCHERICHIA COLI; KINETICS; METABOLISM; SYNTHESIS;

ADENOSINE TRIPHOSPHATE; ENZYME INHIBITORS; ESCHERICHIA COLI; GLUTAMATE-AMMONIA LIGASE; GLUTAMATE-CYSTEINE LIGASE; KINETICS; MODELS, CHEMICAL;

EID: 0033252478     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.63.2248     Document Type: Article

References (17)

1. Griffith, O. W. and Mulcahy, R. T., The enzymes of glutathione synthesis: y-Glutamylcysteine synthetase. Adv. Enzymol. Relat. Areas Mol. Biol., 73, 209-267 (1999).
2. Purich, D. L., Advances in the enzymology of glutamine synthesis. Avd. Enzymol. Relat. Areas Mol. Biol., 72, 9-42 (1998).
3. Bailey, H. H., L-S,β-Buthionine sulfoximine: Historical development and clinical issues. Chem. Biol. Interact., 111-112, 239-254 (1998).
4. Hoerlein, G., Glufosinate (phosphinothricin), a natural amino acid with unexpected herbicidal properties. Rev. Environ. Con-tam. Toxicol., 138, 73-145 (1994).
5. 2+. J. Biol. Chem., 257, 4271-4278 (1982).
6. Colanduoni, J. A. and Villafranca, J. J., Inhibition of Escherichia coli glutamine synthetase by phosphinothricin. Bioorg. Chem., 14, 163-169 (1986).
7. Tokutake, N., Hiratake, J., Katoh, M., Irie, T., Kato, H., and Oda, J., Design, synthesis and evaluation of transition-state analogue inhibitors of Escherichia coli y-glutamylcysteine synthetase. Bioorg. Med. Chem., 6, 1935-1953 (1998).
8. Rudisill, D. E. and Whitten, J. P., Synthesis of (β)-4-oxo-5-phosphononorvaline, an iV-methyl-D-aspartic acid receptor selective β-keto phosphonate. Synthesis, 851-854 (1994).
9. 6P: C, 27.00; H, 3.86; N, 5.36%.
10. 6P: C, 27.39; H, 4.60; N, 5.32%.
11. Bravo, P., Piovosi, E., and Resnati, G., A convenient synthesis of 3-fluorinated 2-oxopropyl sulphoxides from fluorinated lithium acetates and 1-lithioalkyl sulphoxides. Synthesis, 579-582 (1986).
12. F=25.3 Hz, C=N). Anal. Found: C, 41.93; H, 6.09; N, 4.38%. Calcd. for CnH^F.NOsP: C, 42.22; H, 5.79; N, 4.47%.
13. Middleton, W. J., New fluorinating reagents. Dialkylaminosul-fur fluorides. J. Org. Chem., 40, 574-578 (1975).
14. 4P, 367.2162; found, 367.2173.
15. Brolin, S. E., Adenylate kinase (Myokinase). In “Methods of Enzymatic Analysis,” 3rd ed., Vol. 3, eds. Bergmeyer, H. U., Bergmeier, J., and Graßl, M., Verlag Chemie, Weinheim, pp. 540-559 (1983).
16. Rowe, W. B., Ronizo, R. A., and Meister, A., Inhibition of glutamine synthetase by methionine sulfoximine. Studies on methionine sulfoximine phosphate. Biochemistry, 8, 2674-2680 (1969)3.
17. Wedler, F. C., Horn, B. R., and Roby, W. G., Interaction of a new y-glutamyl-phosphate analog, 4-(phosphonoacetyl)-L-a-aminobutyrate, with glutamine synthetase enzymes from Escherichia coli, plant, and mammalian sources. Arch. Biochem. Biophys., 202, 482-490 (1980).