On the absence of stereoselectivity in the catalytic oxidation of alkenes with a surface-bound metalloporphyrin-peptide conjugate

Tetrahedron

Volumn 55, Issue 7, 1999, Pages 1871-1880

  Geier III, G Richard ^a   Lybrand, Terry P ^a   Sasaki, Tomikazu ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

Catalysis; Molecular modeling; Porphyrins; Stereoselectivity

Indexed keywords

ALKENE DERIVATIVE; METALLOPORPHYRIN; PEPTIDE DERIVATIVE;

ARTICLE; CATALYSIS; COMPLEX FORMATION; OXIDATION; PEPTIDE ANALYSIS; PRIORITY JOURNAL; PROTEIN BINDING; STEREOCHEMISTRY;

EID: 0033548111     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01228-9     Document Type: Article

References (30)

1. Geier, G. R.; and Sasaki, T. Tetrahedron 1999, 55, 1859.
2. Geier, G. R. The Preparation of a Metalloporphyrin-Peptide Conjugate Artificial Protein for the Catalytic Oxidation of Alkenes. University of Washington, 1997.
3. (a) Sheldon, R. A., Ed., Metalloporphyrins in Catalytic Oxidations; Marcel Dekker, Inc.: New York, 1994.
4. (b) Montanari, F, and Casella, L, Eds., Metalloporphyrins Catalyzed Oxidations; Kluwer Academic Publishers: Boston, 1994.
5. (c) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; and Brauman, J. I. Science 1993, 261, 1410.
6. (d) Montanari, F.; Banfi, S.; Pozzi, G.; and Quici, S. Rev. Heteroatom Chem. 1992, 6, 94.
7. (e) Meunier, B. Chem. Rev. 1992, 92, 1411.
8. (f) Gunter, M. J.; and Turner, P. Coord. Chem. Rev. 1991, 108, 115.
9. (g) White, P. W. Bioorg. Chem. 1991, 18, 440.
10. Collman, J. P.; Lee, V. J.; Kellen-Yuen, C. J.; Zhang, X.; Ibers, J. A.; and Brauman, J. I. J. Am. Chem. Soc. 1995, 117, 692.
11. Geier, G. R.; and Sasaki, T. Tetrahedron Lett. 1997, 38, 3821.
12. Groves, J. T.; Nemo, T. E.; and Myers, R. S. J. Am. Chem. Soc. 1979, 101, 1032.
13. (a) Groves, J. T.; Kruper, W. J.; Nemo, T. E.; and Myers, R. S. J. Mol. Catal. 1980, 7, 169.
14. (b) Chang, C. K.; and Kuo, M. S; J. Am. Chem. Soc. 1979, 101, 3413.
15. Mansuy, D.; Battioni, P.; Renaud, J. P.; and Guerin, P. J. Chem. Soc. Chem. Commun. 1985, 155.
16. Lieberman, M.; Tabet, M.; and Sasaki, T. J. Am. Chem. Soc. 1994, 116, 5035.
17. (a) Naruta, Y.; Ishihara, N.; Tani, F.; and Maruyama, K. Bull. Chem. Soc. Jpn. 1993, 66, 158.
18. (b) Collman, J. P.; Zhang, X.; Lee, V. J.; and Brauman, J. I. J. Chem. Soc. Chem. Commun. 1992, 1647.
19. (c) Groves, J. T.; and Viski, P. J. Org. Chem. 1990, 55, 3628.
20. (d) Naruta, Y.; Tani, F.; and Maruyama, K. Chem. Lett. 1989, 1269.
21. (e) Groves, J. T.; and Myers, R. S. J. Am. Chem. Soc. 1983, 105, 5791.
22. (a) Collman, J. P.; Lee, V. J.; Zhang, X.; Ibers, J. A.; and Brauman, J. I. J. Am. Chem. Soc. 1993, 115, 3834.
23. (b) Collman, J. P.; Zhang, X.; Lee, V. J.; and Brauman, J. I. J. Chem. Soc. Chem. Commun. 1992, 1647.
24. Rose, E.; Soleilhavoup, M.; Christ-Tommasino, L.; Moreau, G.; Collman, J.P.; Quelquejeu, M.; and Straumanis, A. J. Org. Chem. 1998, 63, 2042.
25. (a) Groves, J. T.; and Nemo, T. E. J. Am. Chem. Soc. 1983, 105, 5786.
26. (b) Naruta, Y.; Ishihara, N.; Tani, F.; and Maruyama, K. J. Am. Chem. Soc. 1991, 113, 6865.
27. (c) Ostovic, D.; He, G. X.; and Bruice, T. C. In Metalloporphyrins in Catalytic Oxidations; Sheldon, R. A., Ed.; Marcel Dekker, Inc.: New York, 1994, 29-68.
28. (d) Ostovic, D.; and Bruice, T. C. Accs. Chem. Res. 1992, 25, 314.
29. Sanders, J. K. M. Chem. Eur. J. 1998, 4, 1378.
30. Computational results obtained using software programs from Biosym/MSI of San Diego-dynamics calculations were done with the Discover® program, using the CFF91 forcefield, and graphical displays were printed out from the Insight® II molecular modeling system.