New simplified inhibitors of EPSP synthase: The importance of ring size for recognition at the shikimate 3-phoshate site

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 23, 1996, Pages 2853-2858

  Peterson, Mark L ^a,b   Corey, Susan D ^a   Font, Jose L ^a,c   Walker, Mark C ^a   Sikorski, James A ^a  

^a MONSANTO COMPANY   (United States)

^b Advanced ChemTech   (United States)

^c Astra Arcus USA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 PHOSPHOSHIKIMATE 1 CARBOXYVINYLTRANSFERASE; ENZYME INHIBITOR; PYRROLE DERIVATIVE;

ARTICLE; BINDING SITE; DRUG SYNTHESIS; ENZYME BINDING; ENZYME INHIBITION; STRUCTURE ACTIVITY RELATION;

EID: 0030568118     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(96)00527-6     Document Type: Article

References (24)

1. 2. (a) Amrhein, N.; Deus, B.; Gehrke, P.; Steinrücken, H. C. Plant Physiol. 1980, 66, 830.
2. (b) Franz, J. E. InThe Herbicide Glyphosate; Grossbard, E.; Atkinson, D. Eds.; Butterworth: Boston, 1985, pp 3-17.
3. (c) Franz, J. E.; Mao, M. K.; Sikorski, J. A. Glyphosate: A Unique Global Herbicide, American Chemical Society Monograph, Washington, D.C., 1996, in press.
4. 3. For reviews see: (a) Sikorski, J. A.; Anderson, K. S.; Cleary, D. G.; Miller, M. J.; Pansegrau, P. D.; Ream, J. E.; Sammons, R. D.; Johnson, K. A. Chemical Aspects of Enzyme Biotechnology: Fundamentals; Baldwin, T. O.; Raushel, F. M.; Scott, A. I. Eds.; Plenum: New York, 1991, pp 23-39.
5. (b) Anderson, K. S.; Johnson, K. A. Chem. Rev. 1990, 90, 1131.
6. 4. (a) Gruys, K. J.; Walker, M. C.; Sikorski, J. A. Biochemistry 1992, 31, 5534.
7. (b) Gruys, K. J.; Marzabadi, M. R.; Pansegrau, P. D.; Sikorski, J. A. Arch. Biochem. Biophys. 1993, 304, 345.
8. 5. (a) Anderson, K. S.; Sikorski, J. A.; Benesi, A. J.; Johnson, K. A. J. Am. Chem. Soc. 1988, 110, 6577.
9. (b) Anderson, K. S.; Sikorski, J. A.; Johnson, K. A. Biochemistry 1988, 27, 7395.
10. 6. (a) Anderson, K. S.; Johnson, K. A. J. Biol. Chem. 1990, 265, 5567.
11. (b) Cleland, W. W. Biochemistry 1990, 29, 3194.
12. 7. Walker, M. C.; Jones, C. R.; Somerville, R. L.; Sikorski, J. A. J. Am. Chem. Soc. 1992, 114, 7601.
13. 8. Alberg, D. G.; Lauhon, C. T.; Nyfeler, R.; Fässler, A.; Bartlett, P. A. J. Am. Chem. Soc. 1992, 114, 3535.
14. 9. Pansegrau, P. D.; Miller, M. J.; Font, J. L.; Ream, J. E.; Sikorski, J. A. Presented at the Fourth Chemical Congress of North America, New York, 1991; Organic Division Poster Presentation No. 29.
15. 10. Leo, G. C.; Castellino, S.; Sammons, R. D.; Sikorski, J. A. Bioorg. Med. Chem. Lett. 1992, 2, 151.
16. 11. Miller, M. J.; Ream, J. E.; Walker, M. C.; Sikorski, J. A. Bioorg. Med. Chem. 1994, 2, 331.
17. 12. Miller, M. J.; Braccolino, D. S.; Cleary, D. G.; Ream, J. E.; Walker, M. C.; Sikorski, J. A. Bioorg. Med. Chem. Lett. 1994, 4, 2605.
18. 13. Miller, M. J.; Cleary, D. G.; Ream, J. E.; Snyder, K. R.; Sikorski, J. A. Bioorg. Med. Chem. 1995, 3, 1685.
19. 14. Shah, A.; Font, J. L.; Miller, M. J.; Ream, J. E.; Walker, M. C.; Sikorski, J. A. Bioorg. Med. Chem. 1996, 4, in press.
20. i'S versus S3P were determined under similar conditions using a fixed PEP concentration of 100 μM, and the data were fit to a model for competitive behavior using GraFit software: Leatherbarrow, R. J. GraFit, Version 2.0, Erithacus Software Ltd,, Staines, U.K., 1990.
21. 16. Anderson, K. S.; Sikorski, J. A.; Johnson, K. A. Biochemistry 1988, 27, 1604.
22. 17. Miller, M. J.; Anderson, K. S.; Braccolino, D. S.; Cleary, D. G.; Gruys, K. J.; Han, C. Y.; Lin, K.-C; Pansegrau, P. D.; Ream, J. E.; Sammons, R. D.; Sikorski, J. A. Bioorg. Med. Chem. Lett. 1993, 3, 1435.
23. 18. Barker, P.; Gendler, P.; Rapoport, H. J. Org. Chem. 1978, 43, 4849.
24. 19. Pansegrau, P. D.; Anderson, K. S.; Widlanski, T.; Ream, J. E.; Sammons, R. D.; Sikorski, J. A.; Knowles, J. R. Tetrahedron Lett. 1991, 32, 2589.