Synthesis of a conformationally restricted substrate analogue of siderophore biosynthetases

Organic Letters

Volumn 3, Issue 4, 2001, Pages 519-521

  Surman, Matthew D ^a   Miller, Marvin J ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AEROBACTIN SYNTHETASE; DRUG DERIVATIVE; LYASE; LYSINE; N(6) ACETYL N(6) HYDROXYLYSINE; N(6)-ACETYL-N(6)-HYDROXYLYSINE; N(OMEGA) ACETYL N(OMEGA) HYDROXYORNITHINE; N(OMEGA)-ACETYL-N(OMEGA)-HYDROXYORNITHINE; ORNITHINE; PALLADIUM; SIDEROPHORE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; ENZYME SPECIFICITY; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

CATALYSIS; LYSINE; MOLECULAR STRUCTURE; ORNITHINE; OXO-ACID-LYASES; PALLADIUM; SIDEROPHORES; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 0035932038     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006813+     Document Type: Article

References (21)

1. Neilands, J. B. Annu. Rev. Biochem. 1981, 50, 715.
2. Lankford, C. E. CRC Crit. Rev. Microbiol. 1973, 2, 273.
3. Crosa, J. H. Annu. Rev. Microbiol. 1984, 38, 69.
4. Neilands, J. B. Annu. Rev. Microbiol. 1981, 36, 285.
5. Roosenberg, J. M.; Lin, Y. M.; Lu, Y.; Miller, M. J. Curr. Med. Chem. 2000, 7, 159.
6. Emery, T. F. Biochemistry 1966, 5, 3694.
7. Ong, D. E.; Emery, T. F. Arch. Biochem. Biophys. 1972, 148, 77.
8. Siegmund, K.; Platter, H. J.; Dickmann, H. Biochim. Biophys. Acta 1991, 1076, 123.
9. Leong, S. A.; Mei, B.; Voisard, C.; Buddle, A.; McEvoy, J.; Wang, J.; Xu, P.; Saville, B. The Development of Iron Chelators for Clinical Use; Bergeron, R. J., Brittenham, G. M., Eds., CRC Press: Boca Raton, 1994; p 187
10. DeLorenzo, V.; Bindereif, A.; Paw, B. H.; Neilands, J. B. J. Bacteriol. 1986, 165, 570.
11. Gross, R.; Engelbrecht, F.; Braun, V. Mol. Gen. Genet. 1985, 201, 204.
12. Murray, G. J.; Clark, G. E. D.; Parniak, M. A.; Viswanatha, T. Can. J. Biochem. 1977, 55, 625.
13. Parniak, M. A.; Jackson, G. E. D.; Murray, G. J.; Viswanatha, T. Biochim. Biophys. Acta 1979, 569, 99.
14. Cycloadduct 1 was prepared as previously reported: Mulvihill, M. J.; Gage, J. L.; Miller, M. J. J. Org. Chem. 1998, 63, 3357.
15. Mulvihill, M. J.; Surman, M. D.; Miller, M. J. J. Org. Chem. 1998, 63, 4874
16. Miller, A.; Procter, G. Tetrahedron Lett. 1990, 31, 1043.
17. Cowart, M.; Bennett, M. J.; Kerwin, J. F., Jr. J. Org. Chem. 1999, 64, 2240.
18. 4 in the ring opening reaction is unclear, in the absence of copper, lower yields of hydroxamic acid 2 were obtained.
19. 1H NMR pattern: δ 1.66 (overlapping ddd, J = 5.7, 5.7, 13.5 Hz, 1H) and 2.35 (overlapping ddd, J = 8.4, 8.4, 13.5 Hz, 1H), clearly displaying cis-coupling.
20. Zhang, D.; Miller, M. J. J. Org. Chem. 1998, 63, 755-759.
21. Appanna, V. D.; Viswanatha, T. FEBS Lett. 1986, 202, 107.