Structural distortion in five-coordinate nitrosyl iron porphyrins. Axial ligand tilting and its effect on equatorial geometry

Journal of the American Chemical Society

Volumn 119, Issue 31, 1997, Pages 7404-7405

  Ellison, Mary K ^a   Scheidt, W Robert ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYRIN DERIVATIVE;

ARTICLE; CRYSTALLOGRAPHY; DRUG STRUCTURE; SOLID STATE;

EID: 0030792299     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971140k     Document Type: Article

References (34)

1. Stamler, J. S.; Singel, S. J.; Loscalzo, J. Science 1992, 258, 1898. Traylor, T. G.; Sharma, V. J. Biochemistry 1992, 31, 2847.
2. Stamler, J. S.; Singel, S. J.; Loscalzo, J. Science 1992, 258, 1898. Traylor, T. G.; Sharma, V. J. Biochemistry 1992, 31, 2847.
3. p, porphyrinato nitrogen.
4. Scheidt, W. R., Frisse, M. E. J. Am. Chem. Soc. 1975, 97, 17.
5. Bohle, D. S.; Hung, C.-H. J. Am. Chem. Soc. 1995, 117, 9584.
6. Nasri, H.; Haller, K. J.; Wang, Y.; Huynh, B. H.; Scheidt, W. R. Inorg. Chem. 1992, 31, 3459.
7. 7 A total of 22 655 reflections were measured: 7890 unique. Complete details are included in the Supporting Information.
8. 7 A total of 22 655 reflections were measured: 7890 unique. Complete details are included in the Supporting Information.
9. 7 A total of 22 655 reflections were measured: 7890 unique. Complete details are included in the Supporting Information.
10. 2) are statistically about twice as large as those based on F, and R factors based on ALL data will be even larger.
11. n notation is that of Enemark and Feltham: Enemark, J. H.; Feltham, R. D. Coord. Chem. Rev. 1974, 13, 339.
12. The number in parentheses following averaged values is the estimated standard deviation calculated on the assumption that the averaged values are drawn from the same population.
13. This tilt might be caused by a very modest intermolecular contact of a methylene carbon atom with the nitrosyl nitrogen: (C(31)⋯N(5) = 3.50 Å, H(31A)⋯N(5) = 2.62 Å). If the Fe-N(5) vector is constrained to be normal to the heme plane, the C(31)⋯N(S) distance would be 3.37 Å and the H(31A)⋯N(5) would be 2.50 Å. An ORTEP illustration of the NO surroundings is available in the Supporting Information.
14. Wayland, B. B.; Olson, L. W. J. Am. Chem. Soc. 1974, 96, 6037.
15. Kon, H.; chikira, M.; Smith, K. M. J. Chem. Soc., Dalton Trans. 1981, 1726.
16. 7 A total of 44 013 reflections were measured; 20 616 unique. Complete details are included in the Supporting Information.
17. Piciulo, P. L.; Scheldt, W. R. J. Am. Chem. Soc. 1976, 98, 1913.
18. Scheidt, W. R.; Brinegar, A. C.; Ferro, E. B.; Kirner, J. F. J. Am. Chem. Soc. 1977, 99, 7315.
19. The experimental results cited below have given a wide range of apparent Fe-C-O angles, (a) Kuriyan, J.; Wilz, S.; Karplus, M.; Petsko, G. A. J. Mol. Biol. 1986, 192, 133. (b) Teng, T.-Y.; Srajer, V.; Moffat, K. Nat. Struct. Biol. 1994, 1, 701. (c) Cheng, X.; Schoenborn, B. P. J. Mol. Biol. 1991, 220, 381. (d) Moore, J. N.; Hansen, P. A.; Hochstrasser, R. M. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 5062. (e) Ormos, P.; Braunstein, D.; Frauenfelder, H.; Hong, M. K.; Lim, S.-L.; Sauke, T. B.; Young, R. D. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 8492. (f) Lim, M.; Jackson, T. A.; Anfinrud, P. A. Science 1995, 269, 962. (g) Ivanov, D.; Sage, J. T.; Keim, M.; Powell, J. R.; Asher, S. A.; Champion, P. A. J. Am. Chem. Soc. 1994, 116, 4139. (h) Quillan, M. L.; Arduini, R. M.; Olson, J. S.; Phillips, G. N., Jr. J. Mol. Biol. 1993, 234, 140. (i) Schlichting, I.; Berendzen, J.; Phillips, G. N., Jr.; Sweet, R. M. Nature 1994, 371, 808.
20. The experimental results cited below have given a wide range of apparent Fe-C-O angles, (a) Kuriyan, J.; Wilz, S.; Karplus, M.; Petsko, G. A. J. Mol. Biol. 1986, 192, 133. (b) Teng, T.-Y.; Srajer, V.; Moffat, K. Nat. Struct. Biol. 1994, 1, 701. (c) Cheng, X.; Schoenborn, B. P. J. Mol. Biol. 1991, 220, 381. (d) Moore, J. N.; Hansen, P. A.; Hochstrasser, R. M. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 5062. (e) Ormos, P.; Braunstein, D.; Frauenfelder, H.; Hong, M. K.; Lim, S.-L.; Sauke, T. B.; Young, R. D. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 8492. (f) Lim, M.; Jackson, T. A.; Anfinrud, P. A. Science 1995, 269, 962. (g) Ivanov, D.; Sage, J. T.; Keim, M.; Powell, J. R.; Asher, S. A.; Champion, P. A. J. Am. Chem. Soc. 1994, 116, 4139. (h) Quillan, M. L.; Arduini, R. M.; Olson, J. S.; Phillips, G. N., Jr. J. Mol. Biol. 1993, 234, 140. (i) Schlichting, I.; Berendzen, J.; Phillips, G. N., Jr.; Sweet, R. M. Nature 1994, 371, 808.
21. The experimental results cited below have given a wide range of apparent Fe-C-O angles, (a) Kuriyan, J.; Wilz, S.; Karplus, M.; Petsko, G. A. J. Mol. Biol. 1986, 192, 133. (b) Teng, T.-Y.; Srajer, V.; Moffat, K. Nat. Struct. Biol. 1994, 1, 701. (c) Cheng, X.; Schoenborn, B. P. J. Mol. Biol. 1991, 220, 381. (d) Moore, J. N.; Hansen, P. A.; Hochstrasser, R. M. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 5062. (e) Ormos, P.; Braunstein, D.; Frauenfelder, H.; Hong, M. K.; Lim, S.-L.; Sauke, T. B.; Young, R. D. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 8492. (f) Lim, M.; Jackson, T. A.; Anfinrud, P. A. Science 1995, 269, 962. (g) Ivanov, D.; Sage, J. T.; Keim, M.; Powell, J. R.; Asher, S. A.; Champion, P. A. J. Am. Chem. Soc. 1994, 116, 4139. (h) Quillan, M. L.; Arduini, R. M.; Olson, J. S.; Phillips, G. N., Jr. J. Mol. Biol. 1993, 234, 140. (i) Schlichting, I.; Berendzen, J.; Phillips, G. N., Jr.; Sweet, R. M. Nature 1994, 371, 808.
22. The experimental results cited below have given a wide range of apparent Fe-C-O angles, (a) Kuriyan, J.; Wilz, S.; Karplus, M.; Petsko, G. A. J. Mol. Biol. 1986, 192, 133. (b) Teng, T.-Y.; Srajer, V.; Moffat, K. Nat. Struct. Biol. 1994, 1, 701. (c) Cheng, X.; Schoenborn, B. P. J. Mol. Biol. 1991, 220, 381. (d) Moore, J. N.; Hansen, P. A.; Hochstrasser, R. M. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 5062. (e) Ormos, P.; Braunstein, D.; Frauenfelder, H.; Hong, M. K.; Lim, S.-L.; Sauke, T. B.; Young, R. D. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 8492. (f) Lim, M.; Jackson, T. A.; Anfinrud, P. A. Science 1995, 269, 962. (g) Ivanov, D.; Sage, J. T.; Keim, M.; Powell, J. R.; Asher, S. A.; Champion, P. A. J. Am. Chem. Soc. 1994, 116, 4139. (h) Quillan, M. L.; Arduini, R. M.; Olson, J. S.; Phillips, G. N., Jr. J. Mol. Biol. 1993, 234, 140. (i) Schlichting, I.; Berendzen, J.; Phillips, G. N., Jr.; Sweet, R. M. Nature 1994, 371, 808.
23. The experimental results cited below have given a wide range of apparent Fe-C-O angles, (a) Kuriyan, J.; Wilz, S.; Karplus, M.; Petsko, G. A. J. Mol. Biol. 1986, 192, 133. (b) Teng, T.-Y.; Srajer, V.; Moffat, K. Nat. Struct. Biol. 1994, 1, 701. (c) Cheng, X.; Schoenborn, B. P. J. Mol. Biol. 1991, 220, 381. (d) Moore, J. N.; Hansen, P. A.; Hochstrasser, R. M. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 5062. (e) Ormos, P.; Braunstein, D.; Frauenfelder, H.; Hong, M. K.; Lim, S.-L.; Sauke, T. B.; Young, R. D. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 8492. (f) Lim, M.; Jackson, T. A.; Anfinrud, P. A. Science 1995, 269, 962. (g) Ivanov, D.; Sage, J. T.; Keim, M.; Powell, J. R.; Asher, S. A.; Champion, P. A. J. Am. Chem. Soc. 1994, 116, 4139. (h) Quillan, M. L.; Arduini, R. M.; Olson, J. S.; Phillips, G. N., Jr. J. Mol. Biol. 1993, 234, 140. (i) Schlichting, I.; Berendzen, J.; Phillips, G. N., Jr.; Sweet, R. M. Nature 1994, 371, 808.
24. The experimental results cited below have given a wide range of apparent Fe-C-O angles, (a) Kuriyan, J.; Wilz, S.; Karplus, M.; Petsko, G. A. J. Mol. Biol. 1986, 192, 133. (b) Teng, T.-Y.; Srajer, V.; Moffat, K. Nat. Struct. Biol. 1994, 1, 701. (c) Cheng, X.; Schoenborn, B. P. J. Mol. Biol. 1991, 220, 381. (d) Moore, J. N.; Hansen, P. A.; Hochstrasser, R. M. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 5062. (e) Ormos, P.; Braunstein, D.; Frauenfelder, H.; Hong, M. K.; Lim, S.-L.; Sauke, T. B.; Young, R. D. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 8492. (f) Lim, M.; Jackson, T. A.; Anfinrud, P. A. Science 1995, 269, 962. (g) Ivanov, D.; Sage, J. T.; Keim, M.; Powell, J. R.; Asher, S. A.; Champion, P. A. J. Am. Chem. Soc. 1994, 116, 4139. (h) Quillan, M. L.; Arduini, R. M.; Olson, J. S.; Phillips, G. N., Jr. J. Mol. Biol. 1993, 234, 140. (i) Schlichting, I.; Berendzen, J.; Phillips, G. N., Jr.; Sweet, R. M. Nature 1994, 371, 808.
25. The experimental results cited below have given a wide range of apparent Fe-C-O angles, (a) Kuriyan, J.; Wilz, S.; Karplus, M.; Petsko, G. A. J. Mol. Biol. 1986, 192, 133. (b) Teng, T.-Y.; Srajer, V.; Moffat, K. Nat. Struct. Biol. 1994, 1, 701. (c) Cheng, X.; Schoenborn, B. P. J. Mol. Biol. 1991, 220, 381. (d) Moore, J. N.; Hansen, P. A.; Hochstrasser, R. M. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 5062. (e) Ormos, P.; Braunstein, D.; Frauenfelder, H.; Hong, M. K.; Lim, S.-L.; Sauke, T. B.; Young, R. D. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 8492. (f) Lim, M.; Jackson, T. A.; Anfinrud, P. A. Science 1995, 269, 962. (g) Ivanov, D.; Sage, J. T.; Keim, M.; Powell, J. R.; Asher, S. A.; Champion, P. A. J. Am. Chem. Soc. 1994, 116, 4139. (h) Quillan, M. L.; Arduini, R. M.; Olson, J. S.; Phillips, G. N., Jr. J. Mol. Biol. 1993, 234, 140. (i) Schlichting, I.; Berendzen, J.; Phillips, G. N., Jr.; Sweet, R. M. Nature 1994, 371, 808.
26. The experimental results cited below have given a wide range of apparent Fe-C-O angles, (a) Kuriyan, J.; Wilz, S.; Karplus, M.; Petsko, G. A. J. Mol. Biol. 1986, 192, 133. (b) Teng, T.-Y.; Srajer, V.; Moffat, K. Nat. Struct. Biol. 1994, 1, 701. (c) Cheng, X.; Schoenborn, B. P. J. Mol. Biol. 1991, 220, 381. (d) Moore, J. N.; Hansen, P. A.; Hochstrasser, R. M. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 5062. (e) Ormos, P.; Braunstein, D.; Frauenfelder, H.; Hong, M. K.; Lim, S.-L.; Sauke, T. B.; Young, R. D. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 8492. (f) Lim, M.; Jackson, T. A.; Anfinrud, P. A. Science 1995, 269, 962. (g) Ivanov, D.; Sage, J. T.; Keim, M.; Powell, J. R.; Asher, S. A.; Champion, P. A. J. Am. Chem. Soc. 1994, 116, 4139. (h) Quillan, M. L.; Arduini, R. M.; Olson, J. S.; Phillips, G. N., Jr. J. Mol. Biol. 1993, 234, 140. (i) Schlichting, I.; Berendzen, J.; Phillips, G. N., Jr.; Sweet, R. M. Nature 1994, 371, 808.
27. The experimental results cited below have given a wide range of apparent Fe-C-O angles, (a) Kuriyan, J.; Wilz, S.; Karplus, M.; Petsko, G. A. J. Mol. Biol. 1986, 192, 133. (b) Teng, T.-Y.; Srajer, V.; Moffat, K. Nat. Struct. Biol. 1994, 1, 701. (c) Cheng, X.; Schoenborn, B. P. J. Mol. Biol. 1991, 220, 381. (d) Moore, J. N.; Hansen, P. A.; Hochstrasser, R. M. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 5062. (e) Ormos, P.; Braunstein, D.; Frauenfelder, H.; Hong, M. K.; Lim, S.-L.; Sauke, T. B.; Young, R. D. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 8492. (f) Lim, M.; Jackson, T. A.; Anfinrud, P. A. Science 1995, 269, 962. (g) Ivanov, D.; Sage, J. T.; Keim, M.; Powell, J. R.; Asher, S. A.; Champion, P. A. J. Am. Chem. Soc. 1994, 116, 4139. (h) Quillan, M. L.; Arduini, R. M.; Olson, J. S.; Phillips, G. N., Jr. J. Mol. Biol. 1993, 234, 140. (i) Schlichting, I.; Berendzen, J.; Phillips, G. N., Jr.; Sweet, R. M. Nature 1994, 371, 808.
28. Jameson, G. B.; Ibers, J. A. In Bioinorganic Chemistry; Bertini, I., Gray, H. B., Lippard, S., Valentine, J. S., Eds.; University Science Books: Mill Valley, CA, 1994; Chapter 4.
29. (a) Balasubramanian, S.; Lambright, D. G.; Boxer S. G. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 4718.
30. (b) Braunstein, D. P.; Chu, K.; Egeberg, K. D.; Frauenfelder, H.; Mourant J. D.; Nienhaus, G. U.; Ormos, P.; Sligar, S. G.; Springer, B. A.; Young, R. D. Biophys. J. 1993, 65, 2447.
31. (c) Li, T.; Quillin M. L.; Phillips, G. N., Jr.; Olson, J. S. Biochemistry 1994, 33, 1433.
32. (d) Springer, B. A.; Sligar, S. G.; Olson, J. S.; Phillips, G. N., Jr. Chem. Rev. 1994, 94, 699.
33. Jewsbury, P.; Yamamoto, S.; Minato, T.; Saito, M.; Kitagawa, T. J. Phys. Chem. 1995, 99, 12677.
34. Ghosh, A.; Bocian, D. F. J. Phys. Chem. 1996, 100, 6363.