Gallium(III) catecholate complexes as probes for the kinetics and mechanism of inversion and isomerization of siderophore complexes

Journal of the American Chemical Society

Volumn 118, Issue 24, 1996, Pages 5712-5721

  Kersting, Berthold ^a   Telford, Jason R ^a   Meyer, Michel ^a   Raymond, Kenneth N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GALLOCATECHIN; SIDEROPHORE;

ARTICLE; COMPLEX FORMATION; ISOMERISM; MODEL; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SPECTROPHOTOMETRY; STEREOCHEMISTRY;

EID: 0030037076     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953545f     Document Type: Article

References (46)

1. Coordination Chemistry of Microbial Iron Transport. 59. Part 58: Hou, Z; Sunderland, C. J.; Nishio, T.; Raymond, K. N. J. Am. Chem. Soc. 1996, 118, 5148.
2. Ecker, D. J.; Loomis, L. D.; Cass, M. E.; Raymond, K. N. J. Am. Chem. Soc. 1988, 110, 2457.
3. Matzanke, B. F.; Müller-Matzanke, G.; Raymond, K. N. Iron Carriers and Iron Proteins. In Physical Bioinorganic Chemistry Series; Loehr, T. M., Ed.; VCH Publishers: New York. 1989; pp 1-121.
4. CRC Handbook of Microbial Iron Chelates; Winkelmann, G., Ed.; CRC Press: Boca Raton, FL, 1991.
5. Raymond, K. N.; Telford, J. R. Siderophore-mediated Iron Transport in Microbes. In Bioinorganic Chemistry An Inorganic Perspective of Life; Kessissoglou, D. P., Ed.; NATO ASI Series; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1995; Vol. 459, pp 25-37.
6. Raymond, K. N.; Müller, G.; Matzanke, B. F. Top. Curr. Chem. 1984, 123, 49.
7. Karpishin, T. B.; Dewey, T. M.; Raymond, K. N. J. Am. Chem. Soc. 1993, 115, 1842.
8. Venuti, M. C.; Rastetter, W. H.; Neilands, J. B. J. Med. Chem. 1979, 22, 123.
9. Nishio, T.; Bryan, B.; Raymond, K. N. Manuscript in preparation.
10. (a) Basolo, F.; Pearson, R. G. Mechanisms of Inorganic Reactions, 2nd ed.; Wiley: New York, 1967.
11. (b) Wilkins, R. G. Kinetics and Mechanism of Reactions of Transition Metal Complexes, 2nd ed.; VCH Publishers: New York, 1991.
12. Fay, R. C.; Piper, T. S. Inorg. Chem. 1964, 3, 348.
13. Fortman, J. J.; Sievers, R. E. Inorg. Chem. 1967, 6, 852.
14. Gordon II, J. G.; Holm, R. H. J. Am. Chem. Soc. 1970, 92, 5319.
15. Bailar, Jr, J. C. J. Inorg. Nucl. Chem. 1958, 8, 165.
16. Rodger, A.; Johnson, B. F. G. Inorg. Chem. 1988, 27, 3062.
17. Garrett, T. M.; McMurry, T. J.; Hosseini, M. W.; Reyes, Z. E.; Hahn, F. E.; Raymond, K. N. J. Am. Chem. Soc. 1991, 113, 2965.
18. McArdle, J. V.; Sofen, S. R.; Cooper, S. R.; Raymond, K. N. Inorg. Chem. 1978, 17, 3075.
19. Borgias, B. A.; Barclay, S. J.; Raymond, K. N. J. Coord. Chem. 1986, 15, 109.
20. Loomis, L. D.; Raymond, K. N. J. Coord. Chem. 1991, 23, 361.
21. Eaton, S. S.; Holm, R. H. J. Am. Chem. Soc. 1971, 93, 4913.
22. Hutchison, J. R.; Gordon, J. G., II; Holm, R. H. Inorg. Chem. 1971, 10, 1004.
23. Eaton, S. S.; Hutchison, J. R.; Holm, R. H.; Muetterties, E. L. J. Am. Chem. Soc. 1972, 94, 6411.
24. Eaton, S. S.; Eaton, G. R.; Holm, R. H.; Muetterties, E. L. J. Am. Chem. Soc. 1973, 95, 1116.
25. Gemlike crystals of 4, 5, 12, and 13 were easily grown by ether diffusion in alcoholic solutions of the metal complexes. However, all of the diffraction patterns obtained from rotation photographs showed diffuse reflections.
26. Spectroscopic Techniques For Organic Chemists; Cooper, J. W., Ed.; John-Wiley & Sons: New York, 1980.
27. Karpishin, T. B.; Gebhard, M. S.; Solomon, E. I.; Raymond, K. N. J. Am. Chem. Soc. 1991, 113, 2977.
28. Albrecht, M.; Franklin, S. J.; Raymond, K. N. Inorg. Chem. 1994, 33, 5785.
29. Karpishin, T. B.; Stack, T. D. P.; Raymond, K. N. J. Am. Chem. Soc. 1993, 115, 6115.
30. 6. The former value is in good agreement with the value obtained from the full line-shape analysis.
31. + cations was observed in the crystal structure of a related gallium(III) complex with tris-(2,3-dihydroxyterephthalamide) coordination. Stack, T. D. P.; Karpishin, T. B.; Raymond, K. N. J. Am. Chem. Soc. 1992, 114, 1512.
32. Garrett, T. M.; Miller, P. W.; Raymond, K. N. Inorg. Chem. 1989, 28, 128.
33. Pecoraro, V. L.; Wong, G. B.; Raymond, K. N. Inorg. Chem. 1982, 21, 2209.
34. Cass, M. E.; Garrett, T. M.; Raymond, K. N. J. Am. Chem. Soc. 1989, 111, 1677.
35. Loomis, L. D.; Hahn, F. E.; Raymond, K. N. Unpublished results.
36. 6 were found to be identical.
37. 6.
38. Glasoe, P. K.; Long, F. A. J. Phys. Chem. 1960, 64, 188.
39. Dynamic Nuclear Magnetic Resonance Spectroscopy, Jackman, L. M., Cotton, F. A., Eds.; Academic Press: New York, 1975.
40. Binsch, G.; Kleier, D. Quantum Chemistry Program Exchange, No. 165. DNMR3 is part of The University of Manitoba NMR Spectral Simulation and Analysis Package. X-11/Motif Version 940101.
41. (a) Scarrow, R. D. Ph.D. Dissertation, University of California at Berkeley, 1985.
42. (b) Turowski, P. N.; Rodgers, S. J.; Scarrow, R. C.; Raymond, K. N. Inorg. Chem. 1988, 27, 474.
43. Franczyk, T. S. Ph.D. Dissertation, University of California at Berkeley, 1991.
44. Abbreviations: acac, 2,4-pentanedione; DCC, 1,3-dicyclohexylcarbodiimide; DCU, 1,3-dicyclohexylurea; DMAP, 4-(dimethylamino)pyridine; NBA, p-nitrobenzyl alcohol; TGG, thioglycerol/glycerol.
45. Karpishin, T. B.; Stack, T. D. P.; Raymond, K. N. J. Am. Chem. Soc. 1993, 115, 182.
46. Weitl, F. L.; Raymond, K. N.; Durbin, P. W. J. Med. Chem. 1981, 24, 203.