Cyclohexenyl and cyclohexylidene inhibitors of 3-Dehydroquinate synthase: Active site interactions relevant to enzyme mechanism and inhibitor design

Journal of the American Chemical Society

Volumn 119, Issue 33, 1997, Pages 7645-7653

  Montchamp, Jean Luc ^a   Frost, J W ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 DEHYDROQUINATE SYNTHASE; CYCLOHEXENE DERIVATIVE; ENZYME INHIBITOR;

ARTICLE; DRUG DESIGN; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME BINDING; ENZYME INHIBITION; ENZYME MECHANISM; STEREOCHEMISTRY;

EID: 0030959729     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961771z     Document Type: Article

References (46)

1. Frey, P. A. In Pyridine Nucleotide Coenzymes Chemical, Biochemical, and Medical Aspects, Part B; Dolphin, D., Poulson, R., Avramovic, O., Eds.; Wiley: New York, 1987; Chapter 13.
2. Knowles, J. R. Aldrichimica Acta 1989, 22, 59.
3. (a) Widlanski, T. S.; Bender, S. L.; Knowles, J. R. J. Am. Chem. Soc. 1987, 109, 1873.
4. (b) Widlanski, T.; Bender, S. L.; Knowles, J. R. J. Am. Chem. Soc. 1989, 111, 2299.
5. (c) Bender, S. L.; Widlanski, T.; Knowles, J. R. Biochemistry 1989, 28, 7560.
6. (d) Widlanski, T.; Bender, S. L.; Knowles, J. R. Biochemistry 1989, 28, 7572.
7. (a) Bartlett, P. A.; Satake, K. J. Am. Chem. Soc. 1988, 110, 1628.
8. (b) Bartlett, P. A.; McLaren, K. L.; Marx, M. A. J. Org. Chem. 1994, 59, 2082.
9. Montchamp, J.-L.; Tian, F.; Hart, M. E.; Frost, J. W. J. Org. Chem. 1996, 61, 3897.
10. Tian, F.; Montchamp, J.-L.; Frost, J. W. J. Org. Chem. 1996, 61, 7373.
11. Hibino, J.; Okazoe, T.; Takai, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5579.
12. (a) Ho, P.-T.; Kolt, R. J. Can. J. Chem. 1982, 60, 663.
13. (b) Falk, J. R.; Abdali, A.; Wittenberger, S. J. J. Chem. Soc., Chem. Commun. 1990, 953.
14. Zwierzak, A.; Kluba, M. Tetrahedron 1971, 27, 3163.
15. Furata, T.; Torigai, H.; Osawa, T.; Iwamura, M. J. Chem. Soc., Perkin Trans. 1 1993, 3139.
16. (a) Thiem, J.; Meyer, B. Org. Magn. Reson. 1978, 11, 50.
17. (b) Kozlov, V. A.; Churusova, S. G.; Ivanchenko, V. I.; Negrebetskii, V. V.; Grapov, A. F.; Mel'nikov, N. N. Zh. Obshch. Khim. 1986, 56, 2013.
18. (c) Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis; Verkade, J. G., Quin, L. D., Eds.; VCH: Deerfield Beach, FL, 1987.
19. Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392.
20. Overman, L. E.; Knoll, F. M. Tetrahedron Lett. 1979, 4, 321.
21. Kalinowski, H.-O. Carbon-13 NMR Spectroscopy; Wiley: Chichester, New York, 1988.
22. Nikolaides, N.; Ganem, B. Tetrahedron Lett. 1989, 30, 1461.
23. Haynes, R. K.; Holden, M. Aust. J. Chem. 1982, 35, 517.
24. Ballesteros, P.; Roberts, B. W.; Wong, J. J. Org. Chem. 1983, 48, 3603.
25. (a) Morrison, J. F.; Walsh, C. T. Adv. Enzymol. 1988, 61, 201.
26. (b) Schloss, J. V. In Target Sites of Herbicide Action; Böger, P., Sandmann, G., Eds.; CRC Press: Boca Raton, FL, 1989.
27. (c) Morrison, J. F.; Stone, S. R. Comments Mol. Cell. Biophys. 1985, 2 , 347.
28. Duggleby, R. G.; Attwood, P. V.; Wallace, J. C.; Keech, D. B. Biochemistry 1982, 21, 3364.
29. Montchamp, J.-L.; Peng, J.; Frost, J. W. J. Org. Chem. 1994, 59, 6999.
30. Montchamp, J.-L.; Frost, J. W. J. Org. Chem. 1994, 59, 7596.
31. Montchamp, J.-L.; Piehler, L. T.; Tolbert, T. J.; Frost, J. W. Bioorg. Med. Chem. Lett. 1992, 2, 1349.
32. Schloss, J. V.; Cleland, W. W. Biochemistry 1982, 21, 4420.
33. (a) Hanozet, G.; Pircher, H.-P.; Vanni, P.; Oesch, B.; Semenza, G. J. Biol. Chem. 1981, 256, 3703.
34. (b) Truscheit, E.; Frommer, W.; Junge, B.; Müller, L.; Schmidt, D. D.; Wingender, W. Angew. Chem., Int. Ed. Engl. 1981, 20, 744.
35. Keenan, M. V.; Alworth, W. L. Biochem. Biophys. Res. Commun. 1974, 57, 500.
36. Kim, C. U.; Lew, W.; Williams, M. A.; Liu, H.; Zhang, L.; Swaminathan, S.; Bischofberger, N.; Chen, M. S.; Mendel, D. B.; Tai, C. Y.; Laver, G.; Stevens, R. C. J. Am. Chem. Soc. 1997, 119, 681.
37. Guranowski, A.; Montgomery, J. A.; Cantoni, G. L.; Chiang, P. K. Biochemistry 1981, 20, 110.
38. Borchardt, R. T.; Keller, B. T.; Patel-Thombre, U. J. Biol. Chem. 1984, 259, 4353.
39. (a) Le Maréchal, P.; Froussios, C.; Level. M.; Azerad, R. Biochem. Biophys. Res. Commun. 1980, 92, 1104.
40. (b) Le Maréchal, P.; Froussios, C.; Level, M.; Azerad, R. Carbohydr. Res. 1981, 94, 1.
41. (a) Montchamp, J.-L.; Piehler, L. T.; Frost, J. W. J. Am. Chem. Soc. 1992, 114, 4453.
42. (b) Piehler, L. T.; Montchamp, J.-L.; Frost, J. W.; Manly, C. J. Tetrahedron 1991, 47, 2423.
43. Myrvold, S.; Reimer, L. M.; Pompliano, D. L.; Frost, J. W. J. Am. Chem. Soc. 1989, 111, 1861.
44. Montchamp, J.-L.; Frost, J. W. J. Am. Chem. Soc. 1991, 113, 6296.
45. Avila, L. Z. Ph.D. Dissertation, Stanford University, CA, 1990.
46. (b) Ames, B. N. Meth. Enzymol. 1966, 8, 115.