175. Model studies for the coenzyme-B12-catalyzed methylmalonyl→succinyl rearrangement. The importance of hydrophobic peripheral associations

Helvetica Chimica Acta

Volumn 79, Issue 8, 1996, Pages 2100-2113

  Darbre, Tamis ^a   Keese, Reinhart ^a   Siljegovic, Vuk ^a   Wolleb Gygi, Annemarie ^a  

^a UNIVERSITY OF BERN   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000965301     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.19960790807     Document Type: Article

References (51)

1. 12', Ed. D. Dolphin, John Wiley, New York, 1982; b) J. Halpern, Science (Washington, D.C.) 1985, 227, 869); c) R G Finke, in 'Molecular Mechanisms in Bioorganic Processes', Eds. C. Bleasdale and B. Golding, The Royal Society of Chemistry, Cambridge, 1990, pp. 244-280.
2. 12', Ed. D. Dolphin, John Wiley, New York, 1982; b) J. Halpern, Science (Washington, D.C.) 1985, 227, 869); c) R G Finke, in 'Molecular Mechanisms in Bioorganic Processes', Eds. C. Bleasdale and B. Golding, The Royal Society of Chemistry, Cambridge, 1990, pp. 244-280.
3. 12', Ed. D. Dolphin, John Wiley, New York, 1982; b) J. Halpern, Science (Washington, D.C.) 1985, 227, 869); c) R G Finke, in 'Molecular Mechanisms in Bioorganic Processes', Eds. C. Bleasdale and B. Golding, The Royal Society of Chemistry, Cambridge, 1990, pp. 244-280.
4. H. Eggerer, E. R. Stadtman, P. Overath, F. Lynen, Biochem. Z. 1960, 333, 1; R. W. Kellermeyer, H. G. Wood, Biochemistry 1962, 1, 1124; R. H. Abeles, B. Zagalak, J. Biol. Chem. 1966, 241, 1245; J. Retey, D. Arigoni, Experientia 1966, 22, 783.
5. H. Eggerer, E. R. Stadtman, P. Overath, F. Lynen, Biochem. Z. 1960, 333, 1; R. W. Kellermeyer, H. G. Wood, Biochemistry 1962, 1, 1124; R. H. Abeles, B. Zagalak, J. Biol. Chem. 1966, 241, 1245; J. Retey, D. Arigoni, Experientia 1966, 22, 783.
6. H. Eggerer, E. R. Stadtman, P. Overath, F. Lynen, Biochem. Z. 1960, 333, 1; R. W. Kellermeyer, H. G. Wood, Biochemistry 1962, 1, 1124; R. H. Abeles, B. Zagalak, J. Biol. Chem. 1966, 241, 1245; J. Retey, D. Arigoni, Experientia 1966, 22, 783.
7. H. Eggerer, E. R. Stadtman, P. Overath, F. Lynen, Biochem. Z. 1960, 333, 1; R. W. Kellermeyer, H. G. Wood, Biochemistry 1962, 1, 1124; R. H. Abeles, B. Zagalak, J. Biol. Chem. 1966, 241, 1245; J. Retey, D. Arigoni, Experientia 1966, 22, 783.
8. a) A. I. Scott, J. Kang, P. Dowd, B. K. Trivedi, Bioorg. Chem. 1980, 9, 227;
9. b) J. H. Grate, J. W. Grate, G. N. Schrauzer, J. Am. Chem. Soc. 1982, 104, 1588;
10. c) P. Dowd, M. Shapiro, Tetrahedron 1984, 40, 3063;
11. d) P. Dowd, B. K. Trivedi, J. Org. Chem. 1985, 50, 206;
12. e) W. M. Best, A. P F. Cook, J. J. Russell, D. A. Widdowson, J. Chem. Soc., Perkin Trans. 1 1986, 1139;
13. f) W. E. Hull, M. Michenfelder, J. Rétey, Eur. J. Biochem. 1988, 173, 191;
14. g) Y. Murakami, Y. Hisaeda, J. Kikuchi, T. Ohno, M. Suzuki, Y. Matsuda, T. Matsuura, J. Chem. Soc., Perkin Trans. 2 1988, 1237;
15. h) Y. Murakami, Y. Hisaeda, T. Ohno, Bioorg. Chem. 1990, 18, 49;
16. i) Y. Murakami, Y Hisaeda, H. Kohno, T. Ohno, T. Nishioka, Bull. Chem. Soc. Jpn. 1992, 65, 3094;
17. j) P. Dowd, B. Wilk, B. K. Wilk, J. Am. Chem. Soc. 1992, 114, 7949;
18. k) A. I. Scott, P. Karuso, H. J. Williams, J. Lally, J. Robinson, G. P. Nayar, ibid. 1994, 116, 777.
19. Y. Zhao, P. Such, J. Rétey, Angew. Chem. 1992, 104, 212; ibid. Int. Ed. 1992, 31, 215.
20. Y. Zhao, P. Such, J. Rétey, Angew. Chem. 1992, 104, 212; ibid. Int. Ed. 1992, 31, 215.
21. B. Beatrix, O. Zelder, F. Kroll, G. Örlygsson, B. T. Golding, W Buckel, Angew. Chem. 1995, 107, 2573; ibid Int. Ed. 1995, 34, 2398.
22. B. Beatrix, O. Zelder, F. Kroll, G. Örlygsson, B. T. Golding, W Buckel, Angew. Chem. 1995, 107, 2573; ibid Int. Ed. 1995, 34, 2398.
23. U. v. Arx, Ph.D. Dissertation, University of Bern, 1985.
24. R. G. Finke, Coord. Chem. Rev. 1984, 54, 1; J. M. Pratt, Chem. Soc Rev. 1985, 14, 161.
25. R. G. Finke, Coord. Chem. Rev. 1984, 54, 1; J. M. Pratt, Chem. Soc Rev. 1985, 14, 161.
26. J. Rétey, Angew. Chem. 1990, 102, 373; ibid. Int. Ed. 1990, 29, 355.
27. J. Rétey, Angew. Chem. 1990, 102, 373; ibid. Int. Ed. 1990, 29, 355.
28. H. Dugas, 'Bioorganic Chemistry - A Chemical Approach to Enzyme Action', 2nd edn., Springer-Verlag, New York, 1989, p 262
29. U. Aeberhard, R. Keese, E. Stamm, U -C. Vögeli, W. Lau, J K. Kochi, Helv. Chim. Acta 1983, 66, 2740.
30. S. Wollowitz, J. Halpern, J. Am. Chem. Soc. 1988, 110, 3112.
31. L. J. Beckwith, D. M. O'Shea, S. Westwood, J. Am. Chem. Soc. 1988, 110, 2565.
32. a) Y. Murakami, Y Hisaeda, T. Ohno, J. Chem. Soc., Perkin Trans. 2 1991, 405;
33. b) M. Fountoulakis, J. Rétey, Chem Ber. 1980, 113, 650.
34. W. P. Jencks, 'Catalysis in Chemistry and Enzymology', Dover Publications, Inc., New York, 1987, p. 393.
35. A. Wolleb-Gygi, T. Darbte, V. Siljegovic, R. Keese, J. Chem. Soc., Chem. Commun. 1994, 835.
36. S. Müller, A. Wolleb, L. Walder, R. Keese, Helv. Chim. Acta 1990, 73, 1659.
37. P. Schulthess, D. Ammann, W. Simon, C Caderas, R. Stepánec, B. Kräutler, Helv Chim. Acta 1984, 67, 1026; V. Siljegovic, Ph.D. Dissertation, University of Bern, 1995.
38. P. Schulthess, D. Ammann, W. Simon, C Caderas, R. Stepánec, B. Kräutler, Helv Chim. Acta 1984, 67, 1026; V. Siljegovic, Ph.D. Dissertation, University of Bern, 1995.
39. Y. Murakami, Y. Hisaeda, A Kajihara, Bull. Chem. Soc. Jpn. 1983, 56, 3642.
40. Y. Murakami, Y. Hisaeda, A. Kajihara, T. Ohno, Bull. Chem. Soc. Jpn. 1984, 57, 405.
41. A. J. Bard, L. R. Faulkner, 'Electrochemical Methods, Fundamentals and Applications', J. Wiley & Sons Inc., New York, 1980, pp. 525-532.
42. R. G. Shorenstein, C. S. Pratt, C.-J. Hsu, T. E Wagner, J Am Chem. Soc. 1968, 90, 6199; F. M. Menger, S. J. Lee, ibid. 1994, 116, 5987.
43. R. G. Shorenstein, C. S. Pratt, C.-J. Hsu, T. E Wagner, J Am Chem. Soc. 1968, 90, 6199; F. M. Menger, S. J. Lee, ibid. 1994, 116, 5987.
44. L. Ernst, J. Chem Soc., Perkin Trans. 1 1984, 2267; S. Muller, Ph. D. Dissertation, University of Bern, 1988; C. Caderas, Ph.D. Dissertation, ETH-Zürich, No. 7822, 1987.
45. L. Ernst, J. Chem Soc., Perkin Trans. 1 1984, 2267; S. Muller, Ph. D. Dissertation, University of Bern, 1988; C. Caderas, Ph.D. Dissertation, ETH-Zürich, No. 7822, 1987.
46. L. Ernst, J. Chem Soc., Perkin Trans. 1 1984, 2267; S. Muller, Ph. D. Dissertation, University of Bern, 1988; C. Caderas, Ph.D. Dissertation, ETH-Zürich, No. 7822, 1987.
47. T. Darbre, O. Zelder, W. Buckel, R. Keese, unpublished results.
48. H. Flohr, W. Pannhorst, J. Rétey, Helv. Chim. Acta 1978, 61, 1565; A. I. Scott, K. Kang, J. Am. Chem. Soc. 1977, 99, 1997.
49. H. Flohr, W. Pannhorst, J. Rétey, Helv. Chim. Acta 1978, 61, 1565; A. I. Scott, K. Kang, J. Am. Chem. Soc. 1977, 99, 1997.
50. A Wolleb, Ph.D. Dissertation, University of Bern, 1993.
51. A. B. Steiger, L. Walder, Helv. Chim. Acta 1992, 75, 90.