Peptide-Based Trihydroxamates as Models for Desferrioxamines. Iron(III)-Holding Properties of Linear and Cyclic N-Hydroxy Peptides with an L-Alanyl-L-alanyl-N-hydroxy-β-alanyl Sequence

Inorganic Chemistry

Volumn 35, Issue 18, 1996, Pages 5173-5180

  Hara, Yukihiro ^a   Akiyama, Masayasu ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001308658     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic951338a     Document Type: Article

References (53)

1. Winkelmann, G., Ed. Handbook of Microbial Iron Chelates; CRC Press: Boca Raton, FL, 1991.
2. Keller-Schierlein, W.; Prelog, V.; Zähner, H. Fortschr. Chem. Org. Naturst. 1964, 22, 279.
3. Neilands, J. B. Science 1967, 156, 1443; Struct. Bonding 1984, 58, 1.
4. Neilands, J. B. Science 1967, 156, 1443; Struct. Bonding 1984, 58, 1.
5. Emery, T. In Metal Ions in Biological Systems; Sigel, H., Ed.; Marcel Dekker: New York, 1978; Vol. 7, Chapter 3.
6. (a) Raymond, K. N.; Müller, G.; Matzanke, B. F. Top. Curr. Chem. 1984, 123, 49.
7. (b) Matzanke, B. F.; Müller-Matzanke, G.; Raymond, K. N. In Iron Carriers and Iron Proteins; Loehr, T. M., Ed.; Physical Bioinorganic Chemistry Series, Vol. 5; VCH Publishers: New York, 1989; Chapter 1.
8. Hider, R. C. Struct. Bonding 1984, 58, 25.
9. Braun, V.; Winkelmann, G. Prog. Clin. Biochem. Med. 1987, 5, 67.
10. Hou, Z.; Whisenhunt, D. W., Jr.; Xu, J.; Raymond, K. N. J. Am. Chem. Soc. 1994, 116, 840. Loomis, L. D.; Raymond, K. N. Inorg. Chem. 1991, 30, 906. Raymond, K. N.; Carrano, J. C. Acc. Chem. Res. 1979, 12, 183.
11. Hou, Z.; Whisenhunt, D. W., Jr.; Xu, J.; Raymond, K. N. J. Am. Chem. Soc. 1994, 116, 840. Loomis, L. D.; Raymond, K. N. Inorg. Chem. 1991, 30, 906. Raymond, K. N.; Carrano, J. C. Acc. Chem. Res. 1979, 12, 183.
12. Hou, Z.; Whisenhunt, D. W., Jr.; Xu, J.; Raymond, K. N. J. Am. Chem. Soc. 1994, 116, 840. Loomis, L. D.; Raymond, K. N. Inorg. Chem. 1991, 30, 906. Raymond, K. N.; Carrano, J. C. Acc. Chem. Res. 1979, 12, 183.
13. Dayan, I.; Libman, J.; Agi, Y.; Shanzer, A. Inorg. Chem. 1993, 32, 1467. Tor, Y.; Libman, J.; Shanzer, A.; Felder, C. E.; Lifson, S. J. Am. Chem. Soc. 1992, 114, 6661.
14. Dayan, I.; Libman, J.; Agi, Y.; Shanzer, A. Inorg. Chem. 1993, 32, 1467. Tor, Y.; Libman, J.; Shanzer, A.; Felder, C. E.; Lifson, S. J. Am. Chem. Soc. 1992, 114, 6661.
15. Akiyama, M.; Katoh, A.; Kato, J.; Takahashi, K.; Hattori, K. Chem. Lett. 1991, 1189. Akiyama, M.; Katoh, A.; Mutoh, T. J. Org. Chem. 1988, 53, 6089.
16. Akiyama, M.; Katoh, A.; Kato, J.; Takahashi, K.; Hattori, K. Chem. Lett. 1991, 1189. Akiyama, M.; Katoh, A.; Mutoh, T. J. Org. Chem. 1988, 53, 6089.
17. Esteves, M. A.; Vaz, M. C. T.; Gonçalves, M. L. S. S.; Farkas, E.; Santos, M. A. J. Chem. Soc., Dalton Trans. 1995, 2565.
18. (a) Bergeron, R. J., Brittenham, G. M., Eds. The Development of Iron Chelators for Clinical Use; CRC Press: Boca Raton, FL, 1994.
19. (b) Martell, A. E., Andersen, W. F., Badman, D. G., Eds. Development of Iron Chelators for Clinical Use; Elsevier/North Holland: New York, 1981.
20. Shimizu, K.; Akiyama, M. J. Chem. Soc., Chem. Commun. 1985, 183.
21. Shimizu, K.; Nakayama, K.; Akiyama, M. Bull. Chem. Soc. Jpn. 1986, 59, 2421.
22. Konetshny-Rapp, S.; Jung, G.; Raymond, K. N.; Meiwes, J.; Zähner, H. J. Am. Chem. Soc. 1992, 114, 2224.
23. Yakirevitch, P.; Rochel, N.; Albrecht-Gary, A. M.; Libman, J.; Shanzer, A. Inorg. Chem. 1993, 32, 1779.
24. Shimizu, K.; Nakayama, K.; Akiyama, M. Bull. Chem. Soc. Jpn. 1984, 57, 2456.
25. Akiyama, M.; Katoh, A.; Iijima, M.; Takagi, T.; Natori, K.; Kojima, T. Bull. Chem. Soc. Jpn. 1992, 65, 1356.
26. Abbreviations are as follows: Ala, L-alanine; β((HO)Ala or β(BnO)-Ala, N-hydroxy- or N-(benzyloxy)-β-alanine; (HO)Gly, N-hydroxyglycine; Boc, tert-butoxycarbonyl; BOP, (benzotriazol-1-yloxy)tris-(dimethylamino)phosphonium hexafluorophosphate(V); dien, diethylenetriamine; EDC, 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide; HOBt, 1-hydroxybenzotriazole; NMM, N-methylmorpholine; TFA, trifluoroacetic acid; AcOSu, N-acetoxysuccinimide; THF, tetrahydrofuran; DMSO, dimethyl sulfoxide; GPC, gel permeation chromatography
27. König, W.; Geiger, R. Chem. Ber. 1970, 103, 788.
28. Castro, B.; Dormoy, J. R.; Evin, G.; Selve, C. Tetrahedron Lett. 1975, 1222.
29. 3CN precluded a solution IR study for the presence of hydrogen bonds.
30. Cram, D. J. Science 1988, 240, 760.
31. Schwarzenbach, G.; Schwarzenbach, K. Helv. Chim. Acta 1963, 46, 1390.
32. Caudle, M. T.; Stevens, R. D.; Crumbliss, A. L. Inorg. Chem. 1994, 33, 843, and 6111.
33. Anderegg, G.; L'Eplattenier, F.; Schwarzenbach, G. Helv. Chim. Acta 1963, 46, 1400, 1409.
34. Martell, A. E.; Motekaitis, R. J. Determination and Use of Stability Constants; VCH Publishers: New York, 1992.
35. (a) Schwarzenbach, G.; Heller, J. Helv. Chim. Acta 1951, 34, 576.
36. (b) Schwarzenbach, G.; Ackermann, H. Helv. Chim. Acta 1947, 30, 1798.
37. Crumbliss, A. L. In Handbook of Microbial Iron Chelates; Winkelmann, G., Ed.; CRC Press: Boca Raton, FL, 1991; Chapter 7.
38. Margerum, D. W.; Rosen, H. M. Inorg. Chem. 1968, 7, 299.
39. Tufano, T. P.; Raymond, K. N. J. Am. Chem. Soc. 1981, 103, 6617.
40. Albrecht-Gary, A. M.; Palanche-Passeron, T.; Rochel, N.; Hennard, C.; Abdallah, M. A. New J. Chem. 1995, 19, 105.
41. Monzyk, B.; Crumbliss, A. L. J. Am. Chem. Soc. 1982, 104, 4921.
42. Biruš, M.; Bradić, Z.; Krznarić, G.; Kujundžić, N.; Pribanić, M.; Wilkins, P. C.; Wilkins, R. G. Inorg. Chem. 1987, 26, 1000.
43. van der Helm, D.; Baker, J. R.; Eng-Wilmont, D. L.; Hossain, M. B.; Loghry, R. A. J. Am. Chem. Soc. 1980, 102, 4224.
44. Wong, G. B.; Kappel, M. J.; Raymond, K. N.; Matzanke, B.; Winkelmann, G. J. Am. Chem. Soc. 1983, 105, 810.
45. Zalkin, A.; Forrester, J. D.; Templeton, D. H. J. Am. Chem. Soc. 1966, 88, 1810.
46. Bickel, H.; Hall, G. E.; Keller-Schierlein, W.; Prelog, V.; Vischer, E.; Wettstein, A. Helv. Chim. Acta 1960, 43, 2129.
47. Leong, J.; Raymond, K. N. J. Am. Chem. Soc. 1975, 97, 293.
48. Müller, G.; Raymond, K. N. J. Bacteriol. 1984, 160, 304.
49. 18 should be called Δ-C-cis,cis instead of N-cis,cis.
50. Borgias, B.; Hugi, A. D.; Raymond, K. N. Inorg. Chem. 1989, 28, 3538.
51. Lindsay, D. G.; Shall, S. Biochem. J. 1971, 121, 737.
52. Irving, H. M.; Miles, M. G.; Pettit, L. D. Anal. Chim. Acta 1967, 38, 475.
53. Gran, G. Analyst 1952, 77, 661.