A theoretical study of the chorismate synthase reaction

Organic Letters

Volumn 3, Issue 26, 2001, Pages 4137-4140

  Dmitrenko, Olga ^a   Wood Jr , Harold B ^b   Bach, Robert D ^a   Ganem, Bruce ^b  

^a UNIVERSITY OF DELAWARE   (United States)

^b Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHORISMATE SYNTHASE; LYASE; RIBOFLAVIN DERIVATIVE;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; METABOLISM; PROTEIN CONFORMATION;

FLAVINS; MODELS, CHEMICAL; PHOSPHORUS-OXYGEN LYASES; PROTEIN CONFORMATION;

EID: 0035961045     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0167964     Document Type: Article

References (21)

1. (a) Haslam, E. Shikimic Acid Metabolism and Metabolites; John Wiley & Sons: New York, 1993;
2. (b) Bentley, R. Crit. Rev. Biochem. Mol. Biol 1990, 25, 307-384.
3. For a recent review, see: Macheroux, P.; Schmid, J.; Amrhein, N.; Schaller, A. Planta 1999, 207, 325-334.
4. Walsh, C. T.; Liu, J.; Rusnak, F.; Sakaitani, M. Chem. Rev. 1990, 90, 1105-1129.
5. Bornemann, S.; Lowe, D. J.; Thorneley, R. N. F. Biochem. Soc. Trans. 1996, 24, 84-88.
6. Bornemann, S.; Lowe, D. J.; Thorneley, R. N. F. Biochemistry 1996, 35, 9907-9916.
7. Westheimer, F. H. Science 1987, 235, 1173-1178.
8. Lloyd, D. J.; Parker, A. J. Tetrahedron Lett. 1970, 5029-5032.
9. Ramjee, M. N.; Coggins, J. R.; Hawkes, T. R.; Lowe, D. J.; Thorneley, R. N. F. J. Am. Chem. Soc. 1991, 113, 8566.
10. Ramjee, M. N.; Balasubramanian, S.; Abell, C.; Coggins, J. R.; Davies, J. M.; Hawkes, T. R.; Lowe, D. J.; Thorneley, R. N. F. J. Am. Chem. Soc. 1992, 114, 3151-3153.
11. Bornemann, S.; Theoclitou, M.-E.; Brune, M.; Webb, M. R.; Thorneley, R. N. F.; Abell, C. Bioorg. Chem. 2000, 28, 191-204.
12. DHCCP lacks the C5-enolpyruvate side chain of EPSP, which is anti to both the phosphate and hydroxyl groups in 1 and would not be expected to exert any stabilizing H-bonding effects. Moreover, the absence of the ether side chain should result in only minor conformational effects on the carbocyclic ring.
13. (a) Becke, A. D. Phys. Rev. A 1988, 37, 785.
14. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B4 1, 785.
15. (c) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
16. (d) Stevens, P. J.; Devlin, F. J.; Chablowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 80, 11623.
17. All calculations used the Gaussian 98 program: Frisch, M. J. et al. Gaussian 98: Gaussian, Inc.: Pittsburgh, PA, 1998.
18. Bach, R. D.; Dmitrenko, O.; Glukhovtsev, M. N. J. Am. Chem. Soc. 2001, 123, 7134-7145.
19. Calculated PA values were based on B3LYP/6-31+G(d,p) total energies and are typically within 1-2% of experimental values.
20. -1) confirmed a TS for proton transfer. The TS was then fully optimized at B3LYP/6-31G(d) with a single point calculation at the B3LYP/ 6-31+G(d,p) level. The estimated classical activation barrier is about 7 kcal/ mol at the B3LYP/3-21G(d,p) and 11 kcal/mol at the B3LYP/6-31+G(d,p)// B3LYP/6-31G(d) level.
21. Kaneda, K.; Kuzuyama, T.; Takagi, M.; Hayakawa, Y.; Seto, H. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 932-937.