Corrigendum to "Asymmetric oxidation catalyzed by myoglobin mutants". [Tetrahedron: Asymmetry 10 (1999) 183] (DOI:10.1016/S0957-4166(98)00498-4);Asymmetric oxidation catalyzed by myoglobin mutants

Tetrahedron Asymmetry

Volumn 10, Issue 1, 1999, Pages 183-192

  Ozaki, Shin Ichi ^a   Yang, Hui Jun ^b   Matsui, Toshitaka ^a   Goto, Yoshio ^b   Watanabe, Yoshihito ^a,b  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^b GRADUATE UNIVERSITY FOR ADVANCED STUDIES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

MUTANT PROTEIN; MYOGLOBIN;

ARTICLE; BIOTRANSFORMATION; CHEMICAL REACTION; ENANTIOMER; OXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0033556669     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.11.044     Document Type: Erratum

References (37)

1. (a) Anderson, B. A.; Hansen, M. M.; Harkness, A. R.; Henry, C. L.; Vicenzi, J. T.; Zmijewski, M. J. J. Am. Chem. Soc. 1995, 117, 12358-12359.
2. (b) Brunel, J.-M.; Diter, P.; Duetsch, M.; Kagan, H. B. J. Org. Chem. 1995, 60, 8086-8088.
3. (c) Stein, K. A.; Toogood, P. L. J. Org. Chem. 1995, 60, 8110-8112.
4. (d) Parmar, V. S.; Singh, A.; Bisht, K. S.; Kumar, N.; Belokon, Y. N.; Kochetkov, K. A.; Ikonnikov, N. S.; Orlova, S. A.; Tararov, V. I.; Saveleva, T. F. J. Org. Chem. 1996, 61, 1223-1227.
5. (e) Itoh, T.; Takagi, Y.; Murakami, T.; Hiyama, Y.; Tsukube, H. J. Org. Chem. 1996, 61, 2158-2163.
6. (f) Hudlicky, T.; Endoma, M. A. A.; Butora, G. Tetrahedron: Asymmetry 1996, 7, 61-68.
7. (g) Huber, P.; Bratovanov, S.; Bienz, S.; Syldatk, C.; Pietzsch, M. Tetrahedron: Asymmetry 1996, 7, 69-78.
8. Morris, D. R.; Hager, L. P. J. Biol. Chem. 1966, 241, 1763-1768.
9. (a) Colonna, S.; Gaggero, N.; Manfredi, A.; Casella, L.; Gullotti, M.; Carrea, G.; Pasta, P. Biochemistry 1990, 29, 10465-10468.
10. (b) Colonna, S.; Gaggero, N.; Casella, L.; Carrea, G.; Pasta, P. Tetrahedron: Asymmetry 1992, 3, 95-106.
11. (c) Colonna, S.; Gaggero, N.; Casella, L.; Carrea, G.; Pasta, P. Tetrahedron: Asymmetry 1993, 4, 1325-1330.
12. (d) Allain, E. J.; Hager, L. P.; Deng, L.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 4415-4416.
13. (e) Dexter, A. F.; Lakner, F. J.; Campbell, R. A.; Hager, L. P. J. Am. Chem. Soc. 1995, 117, 6412-6413.
14. (f) Zaks, A.; Dodds, D. R. J. Am. Chem. Soc. 1995, 117, 10419-10424.
15. (g) Allenmark, S. G.; Andersson, M. Tetrahedron: Asymmetry 1996, 7, 1089-1094.
16. (h) Lakner, F. J.; Cain, K. P.; Hager, L. P. J. Am. Chem. Soc. 1997, 119, 443-444.
17. Butler, A.; Walker, J. V. Chem. Rev. 1993, 93, 1937-1944.
18. Andersson, M.; Willetts, A.; Allenmark, S. J. Org. Chem. 1997, 62, 8455-8458.
19. Antonini, E.; Brunori, M. Hemoglobin and Myoglobin in Their Reactions with Ligands; North-Holland: Amsterdam, 1971.
20. (a) Catalano, C. E.; OrtizdeMontellano, P. R. Biochemistry 1987, 26, 9265-9271.
21. (b) Adachi, S.; Nagano, S.; Ishimori, K.; Watanabe, Y.; Morishima, I.; Egawa, T.; Kitagawa, T.; Makino, R. Biochemistry 1993, 32, 241-252.
22. (c) Rao, S. I.; Wilka, A.; Ortiz de Montellano, P. R. J. Biol. Chem. 1993, 268, 803-809.
23. (d) Matsui, T.; Nagano, S.; Ishimori, K.; Watanabe, Y.; Morishima, I. Biochemistry 1996, 35, 13118-13124.
24. (e) Tschirret-Guth, R. A.; Ortiz de Montellano, P. R. Arch. Biochem. Biophys. 1996, 335, 93-101.
25. (a) Ozaki, S.; Matsui, T.; Watanabe, Y. J. Am. Chem. Soc. 1996, 118, 9784-9785.
26. (b) Ozaki, S.; Matsui, T.; Watanabe, Y. J. Am. Chem. Soc. 1997, 119, 6666-6667.
27. (c) Matsui, T.; Ozaki, S.; Watanabe, Y. J. Biol. Chem. 1997, 272, 32735-32738.
28. 5 incubation system requires 1 h and 10 h, respectively. Our F43H/H64L Mb system produces 7 μmol of the oxidation product of 4 in 30 min, and the linearity of the relationship between time and product formation has been observed for at least 30 min under the reaction conditions.
29. (a) Groves, J. T.; Stern, M. K. J. Am. Chem. Soc. 1988, 110, 8628-8638.
30. (b) Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3528-3634.
31. Miller, V. P.; DePhillis, G. D.; Ferrer, J. C.; Mauk. A. G.; Ortiz de Montellano, P. R. J. Biol. Chem. 1992, 267, 8936-8942.
32. Matsui, T.; Ozaki, S.; Liong, E.; Phillips, G. N.; Watanabe, Y., manuscript in preparation. The coordinate (PDB ID, 1OFJ) is deposited with the Protein Data Bank.
33. Discover and Dock Modules from Molecular Simulation Inc. are used for the studies.
34. For general procedures, see Ausubel, F. M.; Brent, R.; Kingston, R. E.; Moore, D. D.; Seidman, J. G.; Smith, J. A.; Strahl, K. Current Protocols in Molecular Biology; John Wiley & Sons: New York, 1996.
35. (a) Springer, B. A.; Sligar, S. G. Proc. Natl. Acad. Sci. USA 1987, 84, 8961-8965.
36. (b) Wilks, A.; Ortiz de Montellano, P. R. J. Biol. Chem. 1992, 267, 8827-8833.
37. Ozaki, S.; Ortiz de Montellano, P. R. J. Am. Chem. Soc. 1995, 117, 7056-7064.