Structural basis for the inhibition of the biosynthesis of biotin by the antibiotic amiclenomycin

Journal of Biological Chemistry

Volumn 277, Issue 45, 2002, Pages 43352-43358

  Sandmark, Jenny ^a   Mann, Stéphane ^a   Marquet, Andrée ^b   Schneider, Gunter ^a  

^a KAROLINSKA INSTITUTE   (Sweden)

^b SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIZATION; BIOSYNTHESIS; CARRIER CONCENTRATION; CRYSTAL STRUCTURE; ENZYME INHIBITION; ENZYMES;

TRANS ISOMERS;

ANTIBIOTICS;

AMICLENOMYCIN; ANTIBIOTIC AGENT; BIOTIN; PYRIDOXAL 5 PHOSPHATE; SCHIFF BASE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; BINDING SITE; BIOSYNTHESIS; COVALENT BOND; CRYSTAL STRUCTURE; DRUG MECHANISM; ENZYME ACTIVE SITE; ENZYME INACTIVATION; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

AMINOBUTYRIC ACIDS; BIOTIN; CRYSTALLOGRAPHY, X-RAY; ESCHERICHIA COLI; KINETICS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; TRANSAMINASES;

EID: 0037044734     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.M207239200     Document Type: Article

References (43)

1. Eisenberg, M. A. (1973) Adv. Enzymol. 38, 317-371
2. Schneider, G., and Lindqvist, Y. (2001) FEBS Lett. 495, 7-11
3. Marquet, A., Bui, B. T., and Florentin, D. (2001) Vitam. Horm. 61, 51-101
4. Ploux, O., and Marquet, A. (1996) Eur. J. Biochem. 236, 301-308
5. Webster, S. P., Alexeev, D., Campopiano, D. J., Watt, R. M., Alexeeva, M., Sawyer, L., and Baxter, R. L. (2000) Biochemistry 39, 516-528
6. Stoner, G. L., and Eisenberg, M. A. (1975) J. Biol. Chem. 250, 4019-4036
7. Stoner, G. L., and Eisenberg, M. A. (1975) J. Biol. Chem. 250, 4037-4043
8. Baxter, R. L., and Baxter, H. C. (1994) J. Chem. Soc. Commun. 759-760
9. Alexeev, D., Baxter, R. L., Smekal., O., and Sawyer, L. (1995) Structure 3, 1207-1215
10. Huang, W., Jia, J., Gibson, K. J., Taylor, W. S., Rendina, A. R., Schneider, G., and Lindqvist, Y. (1995) Biochemistry 34, 10985-10995
11. Gibson, K. J., Lorimer, G. H., Rendina, A. R., Taylor, W. S., Cohen, G., Gatenby, A. A., Payne, W. G., Roe, C., Lockett, B. A., Nudelman, A., Marcovici, D., Nachum, A., Wexler, B. Marsili, E., Turner, I. M., Howe, L. D., Kalbach, C. E., and Hongji, C. (1995) Biochemistry 34, 10976-10984
12. Käck, H., Gibson, K. J., Lindqvist, Y., and Schneider, G. (1998) Proc. Natl. Acad. Sci. U. S. A. 95, 5495-5500
13. Käck, H., Gibson, K. J., Gatenby, A. A., Schneider, G., and Lindqvist, Y. (1998) Acta Crystallogr. D54, 1397-1398
14. Otsuka, A. J., Buoncristiani, M. R., Howard, P. K., Flamm, J., Johnson, C., Yamamoto, R., Uchida, K., Cook, C., Ruppert, J., and Matsuzaki, J. (1988) J. Biol. Chem. 263, 19577-19585
15. Hayashi, H. (1995) J. Biochem. 118, 463-473
16. Käck, H., Sandmark, J., Gibson, K., Schneider, G., and Lindqvist, Y. (1999) J. Mol. Biol. 291, 857-876
17. Jansonius, J. N. (1998) Curr. Opin. Struct. Biol. 8, 759-769
18. Schneider, G., Käck, H., and Lindqvist, Y. (2000) Structure 8, 1-6
19. Rendina, A. R., Taylor, W. S., Gibson, K., Lorimer, G., Rayner, D., Locket, B., Kranis, K., Wexler, B., Marcovici-Mizrahi, D., Nudelman, A., Nudelman, A., Marsilii, E., Hongii C., Wawrzak, Z., Calabrese, J., Huang, W., Jia, J., Schneider, G., Lindqvist, Y., and Yang, G. (1999) J. Pestic. Sci. 55, 236-247
20. Ploux, O., Breyne, O., Carillon, S., and Marquet, A. (1999) Eur. J. Biochem. 259, 63-70
21. Okami, Y., Kitahara, T., Hamada, M., Naganawa, H., Kondo, S., Maeda, K., Takeuchi, T., and Umezawa, H. (1974) J. Antibiot. 27, 656-664
22. Kern, A., Kabatek, U., Jung, G., Werner, R. G., Poetsch, M., and Zähner, H. (1985) Liebigs Ann. Chem. 5, 877-892
23. Poetsch, M., Zähner, H., Werner, R. G., Kern, A., and Jung, G. (1985) J. Antibiot. 38, 312-320
24. Mann, S., Carillon, S., Breyne, O., and Maequet, A. (2002) Chem. Eur. J. 8, 439-450
25. Hotta, K., Kitahara, T., and Okami, Y. (1975) J. Antibiot. 28, 222-228
26. Izumi, Y., Sato, K., Tani, and Ogata, K. (1973) Agric. Biol. Chem. 37, 2683-2684
27. Leslie, A. (1992) Joint CCP4 and ESF-EACBM Newsletter on Protein Crystallography, vol. 26, Daresbury Laboratory, Warrington, UK
28. Collaborative Computational Project, Number 4 (1994) Acta Crystallogr. D50, 760-763
29. Navaza, J. (1994) Acta Crystallogr. A50, 157-163
30. Murshudov, G. N., Vagin, A. A., and Dodson, E. J. (1997) Acta Crystallogr. D53, 240-258
31. Jones, T. A., Zou, J., Cowan, S., and Kjeldgaard, M. (1991) Acta Crystallogr. A47, 110-119
32. Laskowski, R. A., McArthur, M. W., Moss, D. S., and Thornton, J. M. (1993) J. Appl. Crystallogr. 26, 282-291
33. Kraulis, P. J. (1991) J. Appl. Crystallogr. 24, 946-950
34. Esnouf, R. M. (1997) J. Mol. Graphics Modelling 15, 133-138
35. Merrit, E. A., and Bacon, D. J. (1997) Methods Enzymol. 277, 505-524
36. Metzler, C. M., Visvanath, R., and Metzler, D. E. (1991) J. Biol. Chem. 266, 9374-9381
37. Gehring, H. (1984) Biochemistry 23, 6335-6340
38. Julin, D. A., Wiesinger, H., Toney, M. D., and Kirsch, J. F. (1989) Biochemistry 28, 3815-3821
39. Rando, R. R. (1977) Biochemistry 16, 4604-4610
40. Fu, M., and Silverman, R. B. (1999) Bioorg. Med. Chem. 8, 1581-1590
41. Shah, S. A., Shen, B. W., and Brünger, A. T. (1997) Structure 5 1067-1075
42. Hennig, M., Grimm, B., Contestabile, R., John, R. A. and Jansonius J. N. (1997) Proc. Natl. Acad. Sci. U. S. A. 94, 4866-4871
43. Eads, J. C., Beeby, M., Scapin, G., Yu, T.-W., and Floss, H. G. (1999) Biochemistry 38, 9840-9849