The importance of carboxylate ligands in the differentiation of catalase reactivity from Gif ketonization systems

Tetrahedron Letters

Volumn 37, Issue 8, 1996, Pages 1133-1136

  Barton, Derek H R ^a   Hu, Bin ^a   Taylor, Dennis K ^a   Rojas Wahl, Roy U ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALASE; KETONE;

ARTICLE; ENZYME ACTIVITY; OXIDATION; REACTION ANALYSIS;

EID: 0030065831     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00001-9     Document Type: Article

References (23)

1. G. A. Olah, À. Molnár Hydrocarbon Chemistry Wiley: New York, Chichester, 1995; D. H. R. Barton, D. T. Sawyer, A. E. Martell, ED. The Activation Of Dioxygen and Homogeneous Catalytic Oxidation Plenum Press: New York, London, 1993.
2. G. A. Olah, À. Molnár Hydrocarbon Chemistry Wiley: New York, Chichester, 1995; D. H. R. Barton, D. T. Sawyer, A. E. Martell, ED. The Activation Of Dioxygen and Homogeneous Catalytic Oxidation Plenum Press: New York, London, 1993.
3. D. H. R. Barton, D. Doller Acc. Chem. Res. 1992, 25, 504-512.
4. Other contributions to Gif chemistry see: H.-C. Tung, C. Kang, D. T. Sawyer J. Am. Chem. Soc. 1992, 114, 3445-3455 and references cited therein; U. Schuchardt, W. A. Carvalho, E. V. Spinacé Synlett 1993, 713-718 and references therein; T. Briffaud, C. Larpent, H. Patin J. Chem. Soc. Chem. Commun. 1990, 1193-1194; K.-W. Lee, S. B. Kim, K.-W. Jun, E. K. Shim New. J. Chem., 1993, 17, 409 and references therein.
5. Other contributions to Gif chemistry see: H.-C. Tung, C. Kang, D. T. Sawyer J. Am. Chem. Soc. 1992, 114, 3445-3455 and references cited therein; U. Schuchardt, W. A. Carvalho, E. V. Spinacé Synlett 1993, 713-718 and references therein; T. Briffaud, C. Larpent, H. Patin J. Chem. Soc. Chem. Commun. 1990, 1193-1194; K.-W. Lee, S. B. Kim, K.-W. Jun, E. K. Shim New. J. Chem., 1993, 17, 409 and references therein.
6. Other contributions to Gif chemistry see: H.-C. Tung, C. Kang, D. T. Sawyer J. Am. Chem. Soc. 1992, 114, 3445-3455 and references cited therein; U. Schuchardt, W. A. Carvalho, E. V. Spinacé Synlett 1993, 713-718 and references therein; T. Briffaud, C. Larpent, H. Patin J. Chem. Soc. Chem. Commun. 1990, 1193-1194; K.-W. Lee, S. B. Kim, K.-W. Jun, E. K. Shim New. J. Chem., 1993, 17, 409 and references therein.
7. Other contributions to Gif chemistry see: H.-C. Tung, C. Kang, D. T. Sawyer J. Am. Chem. Soc. 1992, 114, 3445-3455 and references cited therein; U. Schuchardt, W. A. Carvalho, E. V. Spinacé Synlett 1993, 713-718 and references therein; T. Briffaud, C. Larpent, H. Patin J. Chem. Soc. Chem. Commun. 1990, 1193-1194; K.-W. Lee, S. B. Kim, K.-W. Jun, E. K. Shim New. J. Chem., 1993, 17, 409 and references therein.
8. D. H. R. Barton, S. D. Bévière, W. Chavasiri, D. Doller, W. G. Liu, J. H. Reibenspies New. J. Chem. 1992, 16, 1019-1029.
9. C. Bardin, D. H. R. Barton, B. Hu, R. U. Rojas Wahl, D. K. Taylor Tetrahedron Lett. 1994, 35, 5805-5808.; D. H. R. Barton, B. M. Chabot, N. C. Delanghe, B. Hu, V. N. LeGloahec, R. U. Rojas Wahl Tetrahedron Lett. 1995, 36, 7007-7010.
10. C. Bardin, D. H. R. Barton, B. Hu, R. U. Rojas Wahl, D. K. Taylor Tetrahedron Lett. 1994, 35, 5805-5808.; D. H. R. Barton, B. M. Chabot, N. C. Delanghe, B. Hu, V. N. LeGloahec, R. U. Rojas Wahl Tetrahedron Lett. 1995, 36, 7007-7010.
11. 2 is formed.
12. D. H. R. Barton, E. Csuhai, D. Doller, Tetrahedron Lett. 1992, 33, 3413-3416; D. H. R. Barton, E. Csuhai, D. Doller Tetrahedron 1992, 48, 9195-9206.
13. D. H. R. Barton, E. Csuhai, D. Doller, Tetrahedron Lett. 1992, 33, 3413-3416; D. H. R. Barton, E. Csuhai, D. Doller Tetrahedron 1992, 48, 9195-9206.
14. Titrated according to: L. J. Clark Analytical Chemistry 1962, 34, 348-352.
15. 2 in pyridine - acetic acid. D. H. R. Barton, S. D. Bévière Tetrahedron Lett. 1993, 34, 5689-5692.
16. A. Vogel, Vogel's Textbook of Quantitative Chemical Analysis, 5th ed., Longman Scient. & Techn., p. 395; L. W. Winkler, Ber. Dtsch. Chem. Gesell., 1888, 21, 2843.
17. A. Vogel, Vogel's Textbook of Quantitative Chemical Analysis, 5th ed., Longman Scient. & Techn., p. 395; L. W. Winkler, Ber. Dtsch. Chem. Gesell., 1888, 21, 2843.
18. 2.
19. There is precedent for the observed reversibility of oxygen binding at low temperatures. See: N. Kitajima, N. Tamura, H. Amagai, H. Fukui, Y. Moro-oka, Y. Mizutani, T. Kitagawa, R. Mathur, K. Heerwegh, C. A. Reed, C. R. Randall, L. Que Jr., K. Tatsumi J. Am. Chem. Soc. 1994, 116, 9071-9085 and references there cited.
20. D. Coucouvanis, R. A. Reynolds III, W. R. Dunham J. Am. Chem. Soc. 1995, 117, 7570-7571; A. L. Feig, S. J. Lippard Chem. Rev. 1994, 94, 759-805; A. C. Rosenzweig, C. A. Frederick, S. J. Lippard, P. Nordlund Nature 1993, 366, 537-543; K. E. Liu, A. M. Valentine, D. Qiu, D. E. Edmonson, E. H. Appelman, T. G. Spiro, S. J. Lippard J. Am. Chem. Soc. 1995, 117, 4997-4998.
21. D. Coucouvanis, R. A. Reynolds III, W. R. Dunham J. Am. Chem. Soc. 1995, 117, 7570-7571; A. L. Feig, S. J. Lippard Chem. Rev. 1994, 94, 759-805; A. C. Rosenzweig, C. A. Frederick, S. J. Lippard, P. Nordlund Nature 1993, 366, 537-543; K. E. Liu, A. M. Valentine, D. Qiu, D. E. Edmonson, E. H. Appelman, T. G. Spiro, S. J. Lippard J. Am. Chem. Soc. 1995, 117, 4997-4998.
22. D. Coucouvanis, R. A. Reynolds III, W. R. Dunham J. Am. Chem. Soc. 1995, 117, 7570-7571; A. L. Feig, S. J. Lippard Chem. Rev. 1994, 94, 759-805; A. C. Rosenzweig, C. A. Frederick, S. J. Lippard, P. Nordlund Nature 1993, 366, 537-543; K. E. Liu, A. M. Valentine, D. Qiu, D. E. Edmonson, E. H. Appelman, T. G. Spiro, S. J. Lippard J. Am. Chem. Soc. 1995, 117, 4997-4998.
23. D. Coucouvanis, R. A. Reynolds III, W. R. Dunham J. Am. Chem. Soc. 1995, 117, 7570-7571; A. L. Feig, S. J. Lippard Chem. Rev. 1994, 94, 759-805; A. C. Rosenzweig, C. A. Frederick, S. J. Lippard, P. Nordlund Nature 1993, 366, 537-543; K. E. Liu, A. M. Valentine, D. Qiu, D. E. Edmonson, E. H. Appelman, T. G. Spiro, S. J. Lippard J. Am. Chem. Soc. 1995, 117, 4997-4998.