Practical synthesis of hydroxamate-derived siderophore components by an indirect oxidation method and syntheses of a DIG-siderophore conjugate and a biotin-siderophore conjugate

Journal of Organic Chemistry

Volumn 64, Issue 20, 1999, Pages 7451-7458

  Lin, Yun Ming ^a   Miller, Marvin J ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOTIN; DIGOXIGENIN; FERRICHROME; HYDROXAMIC ACID DERIVATIVE; HYDROXYLAMINE; IMINE; ORNITHINE; OXAZIRIDINE DERIVATIVE; SIDEROPHORE; TRIPEPTIDE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROLYSIS; ISOMERISM; OXIDATION; SYNTHESIS;

EID: 0033215405     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990769y     Document Type: Article

References (42)

1. (a) Neilands, J. B. J. Biol. Chem. 1995, 270, 26723.
2. (b) Koster, W.; Braun, V. J. Biol. Chem. 1990, 265, 21407.
3. (a) Wooldridge, K., G., Williams, P. H. FEMS Microbiol. Rev. 1993, 12, 325.
4. (b) Neilands, J. B. Biochem. Biophys. 1993, 302, 1.
5. (a) Connell, N. D.; Nikaido, H. Membrane Permeability and Transport in Mycobacterium tuberculosis. In Tuberculosis: Pathogenesis, Protection, and Control; Bloom, B. R., Ed.; ASM Press: Washington, DC, 1994; Chapter 22.
6. (b) Liu, J.; Rosenberg, E. Y.; Nikaido, H. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 11254.
7. (a) Miller, M. J.; Malouin, F. Acc. Chem. Res. 1993, 26, 241.
8. (b) Miller, M. J.; Malouin, F.; Dolence, E. K.; Gasparski, C. M.; Ghosh, M.; Guzzo, P. R.; Lotz, B. T.; McKee, J. A.; Minnick, A. A.; Teng, M. Iron Transport-Mediated Drug Delivery. In Recent Advances in the Chemistry of Antiinfective Agents; Bently, P. H., Ponsford, R., Eds.; Special Publication No. 119; Royal Society of Chemistry: Royal Society of Chemistry, Cambridge, 1993; Chapter 10.
9. (c) Miller, M. J.; Malouin, F. Siderophore-Mediated Drug Delivery. The Design, Synthesis and Study of Siderophore-Antibiotic and Antifungal Conjugates. In The Development of Iron Chelators for Clinical Use; Bergeron, R. J., Brittenham, G. M., Eds.; CRC Press: Boca Raton, FL, 1994; Chapter 13.
10. (a) Diarra, M. S.; Lavoie, M. C.; Jacques, M.; Darwish, I.; Dolence, E. K.; Dolence, J. A.; Ghosh, A.; Ghosh, M.; Miller, M. J.; Malouin, F. Antimicrob. Agents Chemother. 1996, 40, 2610.
11. (b) Dolence, E. K.; Minnick, A. A.; Miller, M. J. J. Med. Chem. 1990, 33, 461.
12. (c) Ghosh, A.; Miller, M. J. J. Org. Chem. 1993, 58, 7652.
13. (d) McKee, J. A.; Sharma, S. K.; Miller, M. J. Bioconjugate Chem. 1991, 2, 281.
14. (e) Ramurthy, S.; Miller, M. J. J. Org. Chem. 1996, 61, 4120.
15. (f) Ghosh, M.; Miller, M. J. J. Org. Chem. 1994, 59, 1020.
16. (g) Dolence, E. K.; Minnick, A. A.; Lin, C.-E.; Miller, M. J. J. Med. Chem. 1991, 34, 968.
17. Dolence, E. K.; Lin, C.-E.; Miller, M. J. J. Med. Chem. 1991, 34, 956.
18. Xu, Y.; Miller, M. J. J. Org. Chem. 1998, 63, 4314.
19. Miller, M. J. Chem. Rev. 1989, 89, 1563
20. (a) Lee, B. H.; Miller, M. J. J. Org. Chem. 1983,48, 24.
21. (b) Lee, B. H.; Miller, M. J.; Prody, C. A.; Neilands, J. B J. Med. Chem. 1985, 28, 317.
22. (c) Lee, B. H.; Miller, M. J.; Prody, C. A.; Neilands, J. B.J. Med. Chem. 1985, 28, 323.
23. (d) Lee, B. H.; Gerfen, G. J.; Miller, M. J. J. Org. Chem. 1984, 49, 2418.
24. (e) Maurer, P. J.; Miller, M. J. J. Am. Chem. Soc. 1982, 104, 3096.
25. (f) Maurer, P. J.; Miller, M. J. J. Am. Chem. Soc. 1983, 105, 240.
26. (g) Maurer, P. J.; Miller, M. J. J. Org. Chem. 1981, 46, 2835.
27. (a) Hu, J.; Miller, M. J. J. Org. Chem. 1994, 59, 4858.
28. (b) Hu, J.; Miller, M. J. J. Am. Chem. Soc. 1997, 119, 3462.
29. (a) Bergeron, R. J.; Phanstiel IV, O. J. Org. Chem. 1992, 57, 7140.
30. (b) Milewska, M. J.; Chimiak, A, Synthesis 1990, 233.
31. (a) Wang, Q. X.; King, J.; Phanstiel IV, O. J. Org. Chem. 1997, 62, 8104.
32. (b) Phanstiel, IV, O.; Wang, Q. X.; Powell, D. H.; Ospina, M. P.; Leeson, B. A. J. Org. Chem. 1999, 64, 803.
33. Naegeli, H.-U.; Keller-Schierlein, W. Helv. Chim. Acta 1978, 61, 2088.
34. Zhang, L.; Finn, J. M. J. Org. Chem. 1995, 60, 5719.
35. Ottenheijm, H. C. J.; Herscheid, J. D. M. Chem. Rev. 1986, 86, 697.
36. Sharman, G. J.; Williams, D. H.; Ewing, D. F.; Ratledge, C. Chem. Biol. 1995, 2, 553.
37. (a) Wittman, M. D.; Halcomb, R. L.; Danishefsky, S. J. J. Org. Chem. 1990, 55, 1981.
38. (b) Gould, S. J.; Ju, S. J. Am. Chem. Soc. 1989, 111, 2329.
39. Bodanszky, M. "Principles of Peptide Synthesis," 2nd Ed., Springer-Verlag: New York, 1993.
40. Klausner, Y. S.; Bodanszky, M. Bioorg. Chem. 1973, 2, 354.
41. Hu, J.; Miller, M. J. J. Am. Chem. Soc. 1997, 119, 3462.
42. 2O gradient (10% to 90%, with 0.1% TFA added to both solvents) was used as the mobile phase with a flow rate of 1.0 mL/min.