Lariat Ether Carboxylic Acids as Ionizable Hosts in the Second Coordination Sphere of the Siderophore Ferrioxamine B in Chloroform

Inorganic Chemistry

Volumn 37, Issue 7, 1998, Pages 1438-1445

  Batinic Haberle I ^a   Spasojevic I ^a   Jang, Y ^b   Bartsch, R A ^b   Crumbliss, A L ^a  

^a DUKE UNIVERSITY   (United States)

^b TEXAS TECH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042404267     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic970925o     Document Type: Article

References (58)

1. Crumbliss, A. L. In Handbook of Microbial Iron Chelates; Winkelmann, G., Ed.; CRC Press: Boca Raton, FL, 1991; p 177.
2. Raymond, K. N.; Telford, J. R. In Bioinorganic Chemistry: An Inorganic Perspective of Life; Kessissoglou, D. P., Ed.; NATO ASI Series C: Mathematical and Physical Sciences, 459; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1995; p 25.
3. Telford, J. R.; Raymond, K. N. Vol. 1, Molecular Recognition: Receptors for Cationic Guests; Gokel, G. W., Vol. Ed.; In Comprehensive Supramolecular Chemistry; Lehn, J.-M. Exec. Ed.; Pergamon Press: London, 1996; p 245.
4. Albrecht-Gary, A.-M.; Crumbliss, A. L. In Iron Transport and Storage in Microorganisms, Plants and Animals; Sigel, A., Sigel, H., Eds.; Metal Ions in Biological Systems 35; M. Dekker: New York, 1998; p 239.
5. (a) Crichton, R. R. Inorganic Biochemistry of Iron Metabolism, Ellis Horwood: New York, 1991; Chapter 3.
6. (b) Braun, V.; Hantke, K.; Eick-Helmerich, K.; Koster, W.; Pressler, U.; Sauer, M.; Schaeffer, S.; Schoeffler, H.; Staudenmaier, H.; Zimmermann, L. In Iron Transport in Microbes, Plants and Animals; Winkelmann, G., van der Helm, D., Nielands, J. B., Eds.; VCH: Weinheim, 1987; p 35.
7. (c) Braun, V.; Hantke, K. In CRC Handbook of Microbial Iron Chelates; CRC Press: Boca Raton, FL, 1991; p 107.
8. (d) Earhart, C. In Iron Transport in Microbes, Plants and Animals; Winkelmann, G., van der Helm, D., Nielands, J. B., Eds.; VCH: Weinheim, 1987; p 67.
9. (e) Chenault S. S.; Earhart, C. F. Mol. Microbiol. 1991, 5, 1405.
10. (f) Hantke, K. Proteins of Iron Storage and Transport; Elsevier/North Holland: Amsterdam, 1985; p 231.
11. (g) Braun, V.; Gunter, K.; Hantke, K. Biol. Met. 1991, 4, 14.
12. (h) Koster, W. Biol. Met. 1991, 4, 23.
13. (i) Lesuisse, E.; Labbe, P. J. Gen. Microbiol. 1989, 135, 257.
14. (j) Matzanke, B. F.; Berner, I.; Bill, E.; Trautwein, A. X.; Winkelmann, G. Biol. Met. 1991, 4, 181.
15. (k) Baeumler A. J.; Hantke, K. Mol. Microbiol. 1992, 6, 1309.
16. (l) Kachadourian, R.; Dellagi, A.; Laurent, J.; Bricard, L.; Kunesch, G.; Expert, D. BioMetals 1996, 9, 143.
17. (m) Jiang, X.; Payne, M. A.; Cao, Z.; Foster, S. B.; Feix, J. B.; Newton, S. M. C.; Klebba, P. E. Science 1997, 276, 1261.
18. Mueller, G.; Matzanke, B. F.; Raymond, K. N. J. Bacteriol. 1984, 160, 313.
19. Fyles, T. M. Top. Inclusion Sci. 1991, 2, 59.
20. Hiraoka, M., Ed. Crown Ethers and Analogous Compounds: Studies in Organic Chemistry; Elsevier: Amsterdam, 1992; Vol. 45.
21. Cox, B.; Schneider, H. Coordination and Transport Properties of Macrocyclic Compounds in Solution; Elsevier: Amsterdam, 1992.
22. Inoue Y., Gokel, G. W., Eds. Cation Binding by Macromolecules; Marcel Dekker Inc.: New York and Basel, 1990.
23. Crumbliss. A. L.; Batinić-Haberle, I.; Spasojević, I. Pure Appl. Chem. 1996, 68, 1225.
24. Spasojević, I.; Batinić-Haberle, I.; Choo, P. L.; Crumbliss, A. L. J. Am. Chem. Soc. 1994, 116, 5714.
25. Batinić-Haberle, I.; Spasojević, I.; Crumbliss, A. L. Inorg. Chem. 1996, 35, 2352.
26. Caldwell, C. D.; Crumbliss, A. L. Inorg. Chem., accepted for publication.
27. Batinić-Haberle, I.; Crumbliss, A. L. Inorg. Chem. 1995, 34, 928.
28. Batinić-Haberle, I.; Spasojević, I.; Bartsch, R. A.; Crumbliss, A. L. J. Chem. Soc. Dalton Trans. 1995, 2503.
29. Ovchinikov, Yu. A.; Ivanov, V. T.; Shkrob, A. M. Membrane-Active Complexones; Elsevier Scientific Publishing: Amsterdam, 1974.
30. Cox, B.; Schneider, H. Coordination and Transport Properties of Macrocyclic Compounds in Solution; Elsevier: Amsterdam, 1992.
31. Batinić-Haberle, I.; Spasojević, I.; Crumbliss, A. L. Inorg. Chim. Acta 1997, 260, 35.
32. Gokel, G. W. In Lariat Ethers in Inclusion Compounds, Vol. 4, Key Organic Host Systems; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Eds.; Oxford University Press: Oxford, 1941; p 283.
33. Gokel, W.; Nakano, A. In Crown Compounds. Towards Future Applications; Cooper, S. R., Ed.; VCH Publishers: New York, 1992; p 1.
34. Gokel, G. W. Chem. Soc. Rev. 1992, 21, 39.
35. Weber, E. New Development in Crown Ether Chemistry: Lariat, Spherand and Second-Sphere Complexes in Crown Ethers und Analogues; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1989.
36. Gokel, G. W.; Arnold, K. A.; Delgado, M.; Echeverria, L.; Gatto, V. J.; Gustowski, D. A.; Hernandez J.; Kaifer, A.; Miller, S. R.; Echegoyen, L. Pure Appl. Chem. 1988, 60, 461.
37. Li, Y.; Gokel, G.; Hernandez, J.; Echegoyen, L. J. Am. Chem. Soc. 1994, 116, 3087.
38. Tsukube, H. Coord. Chem. Rev. 1996, 148, 1.
39. Potvin, P. G.; Lehn, J.-M. In Progress in Macrocyclic Chemistry. Vol. 3; Izatt, R M., Christensen, J. J., Eds.; Wiley: New York, 1987: p 167.
40. Koszuk, J. F.; Czech, B. P.; Walkowiak, W.; Babb, D. A.; Bartsch, R. A. J. Chem. Soc., Chem. Commun. 1984, 1504.
41. Strzelbicki, J.; Charevicz, A.; Bartsch, R. A. J. Inclusion Phenom. 1988, 6, 57.
42. Leonard, N. J.; Fox, R. C.; Oki, M. J. Am. Chem. Soc. 1954, 76, 5708.
43. Czech, B.; Babb, D. A.; Bartsch, R. A. Org. Prep. Proced. Int. 1983, 15, 29.
44. Under these conditions, the ethyl ester which was formed by the alkylation reaction was automatically hydrolyzed to the desired carboxylic acid.
45. Leggett, D. J., Ed. Computational Methods for the Determination of Formation Constants; Plenum Press: New York, 1985: p 37.
46. May, P. M.; Williams, D. R. Talanta 1982, 29, 249.
47. Rorabacher, D. B.; MacKellar, W. J.; Shu, F. R.; Sister Bonavita, M. Anal. Chem. 1971, 43, 561.
48. Evers, A.; Hancock, R. D.; Martell, A. E.; Motekaitis, R. J. Inorg. Chem. 1989, 28, 2189.
49. Stability Constants of Metal Complexes. Part A: Inorganic Ligands; Houfeldt, E., Compiler: IUPAC Chemical Data Series 21: Pergamon Press: Oxford, 1982.
50. Monzyk, B.; Crumbliss, A. L. J. Am. Chem. Soc. 1982, 104, 4921.
51. Izatt, R M.; Bradshaw, J. S.; Nielsen. S. A.; Lamb, J. D.; Christensen, J. J. Chem. Rev. 1985, 85, 271.
52. Izatt, R. M.; Pawlak, K.; Bradshaw, J. S.; Bruening, R. L. Chem. Rev. 1991, 91, 1721.
53. Lamb, J. D.; Christensen, J. J.; Izatt, S. R.; Bedke, K.; Astin, M. S.; Izatt, R. M. J. Am. Chem. Soc. 1980, 102, 3399.
54. Christensen, J. J.; Lamb, J. D.; Izatt, S. R.; Starr, S. E.; Weed, G. C.; Astin, M. S.; Stitt, B. D.; Izatt, R. M. J. Am. Chem. Soc. 1978, 100, 3219.
55. Beresdorf, G. D.; Stoddart, J. F. Tetrahedron Lett. 1980, 21, 867.
56. Jazimirski, K. B. Thermochemie von Komplexverbindungen; Akademie-Verlag: Berlin, 1956.
57. Vasil'ev, V. P.; Zolotarev, E. K.; Kaustinskii, A. F.; Mishchenko, K. P.; Podgornaya, E. A.; Jazimirski, K. B. Zh. Fiz. Khim. 1960, 34, 1763; Russ. J. Phys. Chem. (Engl. transl.) 1960, 34, 840.
58. Vasil'ev, V. P.; Zolotarev, E. K.; Kaustinskii, A. F.; Mishchenko, K. P.; Podgornaya, E. A.; Jazimirski, K. B. Zh. Fiz. Khim. 1960, 34, 1763; Russ. J. Phys. Chem. (Engl. transl.) 1960, 34, 840.