2-oxo-3-alkynoic acids, universal mechanism-based inactivators of thiamin diphosphate-dependent decarboxylases: Synthesis and evidence for potent inactivation of the pyruvate dehydrogenase multienzyme complex

Biochemistry

Volumn 36, Issue 26, 1997, Pages 8071-8081

  Brown, Angela ^a   Nemeria, Natalia ^a   Yi, Jizu ^a   Zhang, Deqi ^a   Jordan, William B ^a   Machado, Rosane S ^b   Guest, John R ^b   Jordan, Frank ^a  

^a RUTGERS UNIVERSITY   (United States)

^b UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

COCARBOXYLASE; DECARBOXYLASE INHIBITOR; PYRUVATE DEHYDROGENASE COMPLEX;

ARTICLE; ENZYME INACTIVATION; ENZYME INHIBITOR INTERACTION; ESCHERICHIA COLI; INHIBITION KINETICS; LACTOBACILLUS PLANTARUM; NONHUMAN; PRIORITY JOURNAL; SACCHAROMYCES CEREVISIAE;

BACTERIAL PROTEINS; ENZYME ACTIVATION; ESCHERICHIA COLI; FATTY ACIDS, UNSATURATED; FUNGAL PROTEINS; KINETICS; LACTOBACILLUS; PYRUVATE DECARBOXYLASE; PYRUVATE DEHYDROGENASE COMPLEX; PYRUVATE OXIDASE; SACCHAROMYCES CEREVISIAE; THIAMINE PYROPHOSPHATE;

ESCHERICHIA COLI; LACTOBACILLUS PLANTARUM; SACCHAROMYCES CEREVISIAE;

EID: 0030875135     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi970094y     Document Type: Article

References (56)

1. Adamson, S. R., & Stevenson, K. J. (1981) Biochemistry 20, 3418-3424.
2. Adamson, S. R., Robinson, J. A., & Stevenson, K. J. (1984) Biochemistry 23, 1269-1274.
3. Annan, N., Paris, R., & Jordan, F (1989) J. Am. Chem. Soc. 111, 8895-8901.
4. Apfel, M. A., Ikeda, B. H., Speckhard, D. C., & Frey, P. A. (1984) J. Biol. Chem. 259, 2905-2909.
5. Baburina, I. (1996) Ph.D. Dissertation, Rutgers University Graduate Faculty, Newark, NJ.
6. Baburina, I., Gao, Y., Hu, Z., Hohmann, S., Furey, W., & Jordan, F. (1994) Biochemistry 33, 5630-5635.
7. Baburina, I., Moore, D. J., Volkov, A., Kahyaoglu, A., Jordan, F., & Mendelsohn, R. (1996) Biochemistry 35, 10249-10255.
8. Bantel-Schaal, U., & Bisswanger H. (1980) Hopper-Seyler's Z. Physiol. Chem. 361, 1265-1266.
9. Bisswanger, H. (1980) Biochem. Biophys. Res. Commun. 95, 513-519.
10. Bisswanger, H. (1981) J. Biol. Chem. 256, 815-822.
11. Bisswanger, H., & Henning, U. (1971) Eur. J. Biochem. 24, 376-384.
12. Bremer, J. (1969) Eur. J. Biochem. 8, 535-540.
13. Chiu, C. C., & Jordan, F. (1994) J. Org. Chem. 59, 5763-5766.
14. de Graaf-Hess & de Kok, A. (1982) FEBS Lett. 143, 261-264.
15. Dennert, G., & Eaker, D. (1970) FEBS Lett. 6, 257-261.
16. Dikdan, G. (1994) Ph.D. Dissertation, Rutgers University Graduate Faculty, Newark, NJ.
17. Farrenkopf, B., & Jordan, F. (1992) Protein Expression Purif. 3, 101-107.
18. Flournoy, D. S., & Frey, P. A. (1989) Biochemistry 28, 9594-9602.
19. Gunsalus, I. C. (1954) in The Mechanism of Enzyme Action (McElvoy, W. D., & Glass, B., Eds.) pp 545-580, Johns Hopkins, Baltimore, MD.
20. Gutowski, J. A., & Lienhard, G. E. (1976) J. Biol. Chem. 251, 2863-2866.
21. Henning, J., Kern G., Neef, H., Bisswanger H., & Hübner G. (1996) in Biochemistry and Physiology of Thiamin Diphosphate Enzymes (Bisswanger, H., & Schellenberger, A., Eds.) pp 235-243, A. u. C. Intemann, Prien, Germany.
22. Holzer, H., Shultz, G., Villar-Palasi, C., & Juntgen-Sell, J. (1956) Biochem. Z. 327, 331-344.
23. Hübner, G., Weidhase, R., & Schellenberger, A. (1978) Eur. J. Biochem. 92, 175-181.
24. Jackson, P. H., & Singer, T. P. (1983) J. Biol. Chem. 258, 1857-1865.
25. Jordan, F., Adams, J., Farzami, B., & Kudzin, Z. H. (1986) J. Enzyme Inhib. 1, 139-149.
26. Kitz, R., & Wilson, I. B. (1962) J. Biol. Chem. 237, 3245-3249.
27. Kluger, R., & Pike, D. C. (1977) J. Am. Chem. Soc. 99, 4504-4506.
28. Koike, M., Reed, L., & Carroll, W. R. (1960) J. Biol. Chem. 235, 1924-1930.
29. Kuo, D. J., & Jordan, F. (1983) Biochemistry 22, 3735-3740.
30. Kuwana, H., Caroline, D. F., Harding, R. W., & Wagner, R. P. (1968) Arch. Biochem. Biophys. 128, 184-193.
31. Lowe, P. N., & Perham, R. N. (1984) Biochemistry 23, 91-97.
32. Lowe, P. N., Leeper, F. J., & Perham, R. N. (1983) Biochemistry 22, 150-157.
33. Machado, R. S. (1993) Ph.D. Thesis, University of Sheffield, Sheffield, U.K.
34. Machado, R. S., Clark, D. P., & Guest, J. R. (1992) FEMS Microbiol. Lett. 100, 243-248.
35. Maldonado, M. E., Oh, K., & Frey, P. A.(1972) J. Biol. Chem. 247, 2711-2716.
36. Massey, V. (1963) in The Enzymes (Boyer, P. D., Lardy, H., & Myrbaeck, K., Eds.) 2nd ed., Vol. 7, pp 275-305, Academic Press, New York.
37. McNally, A. J., Motter, K., & Jordan, F. (1995) J. Biol. Chem. 270, 19736-19743.
38. Menon-Rudolph, S., Nishikawa, S., Zeng, X., Jordan, F. (1992) 114, 10110-10112.
39. Moe, O. A., & Hammes, G. G. (1974) Biochemistry 13, 2547-2552.
40. Reed, L. J. (1974) Acc. Chem. Res. 7, 40-47.
41. Russell, G. C., Machado, R. S., & Guest, J. R. (1992) Biochem. J. 287, 611-619.
42. Schwartz, E. R., & Reed, L. J. (1970) Biochemistry 9, 1434-1439.
43. Schwartz, E. R., Old, L. O., & Reed, L.(1968) Biochem. Biophys. Res. Commun. 31, 495-500.
44. Schonbrunn-Hanebeck, E., Laber, B., & Amrhein, N. (1990) Biochemistry 29, 4880-4885.
45. Shepherd, G. B., & Hammes, G. G. (1976) Biochemistry 15, 311-317.
46. Spinka, M., & Hübner, G. (1996) in Biochemistry and Physiology of Thiamin Diphosphate Enzymes (Bisswanger, H., & Schellenberger, A., Eds.) pp 186-194, A. u. C. Intemann, Prien, Germany.
47. Stephens, P. E., Darlison, M. G., Lewis, H. M., & Guest, J. R.-(1983a) Eur. J. Biochem. 133, 155-162.
48. Stephens, P. E., Darlison, M. G., Lewis, H. M., & Guest, J. R.-(1983b) Eur. J. Biochem. 133, 481-489.
49. Stephens, P. E., Lewis, H. M., Darlison, M. G., & Guest, J. R. (1983c) Eur. J. Biochem. 135, 519-527.
50. Stevenson, K. J., Hale, G., & Perham, R. N. (1978) Biochemistry 17, 2189-2192.
51. Torchinsky (1977) in Sulfur in Proteins (Metzler, D., Ed.) p 17, Pergamon Press, Oxford, U.K.
52. Vogel, O., & Henning, U. (1971) Eur. J. Biochem. 133, 155-162.
53. Westerfeld, N. W. (1945) J. Biol. Chem. 161, 495-502.
54. Yi, J., Nemeria, N., McNally, A., Jordan, F., Machado, R. S., & Guest, J. R. (1996) J. Biol. Chem. 271, 33192-33200.
55. Zeng, X., Chung, A., Haran, M., & Jordan, F. (1991) J. Am. Chem. Soc. 113, 5842-5849.
56. Zeng, X., Farrenkopf, B., Hohmann, S., Dyda, F., Furey, W., & Jordan, F. (1993) Biochemistry 32, 2704-2709.