A chemically synthesized version of the insect antibacterial glycopeptide, diptericin, disrupts bacterial membrane integrity

Biochemistry

Volumn 38, Issue 36, 1999, Pages 11700-11710

  Winans, Katharine A ^a   King, David S ^a   Rao, Vikram R ^a   Bertozzi, Carolyn R ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; DIPTERICIN; GLYCOPEPTIDE; POLYPEPTIDE; PROLINE; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; ARTICLE; BACTERIAL GROWTH; BACTERIAL MEMBRANE; CARBON NUCLEAR MAGNETIC RESONANCE; CARBOXY TERMINAL SEQUENCE; CIRCULAR DICHROISM; CONTROLLED STUDY; DRUG MECHANISM; ESCHERICHIA COLI; GLYCOSYLATION; GROWTH INHIBITION; HEMOLYMPH; MEMBRANE PERMEABILITY; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

AMINO ACID SEQUENCE; ANIMALS; ANTI-BACTERIAL AGENTS; CELL MEMBRANE PERMEABILITY; CIRCULAR DICHROISM; DROSOPHILA PROTEINS; ESCHERICHIA COLI; GLYCOPEPTIDES; INSECT PROTEINS; INSECTS; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; MOLECULAR SEQUENCE DATA; PROTEIN CONFORMATION; SEQUENCE HOMOLOGY, AMINO ACID;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; HEXAPODA; INSECTA;

EID: 0033533481     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi991247f     Document Type: Article

References (58)

1. Broddefalk, J., Nilsson, U., and Kihlberg, J. (1994) J. Carbohydr. Chem. 13, 129-132.
2. Hultmark, D. (1993) Trends Genetics 9, 178-83.
3. Boman, H. G., and Hultmark, D. (1987) Annu. Rev. Microbiol. 41, 103-26.
4. Piers, K. L., and Hancock, R. E. (1994) Mol. Microbiol. 12, 951-8.
5. Bulet, P., Hegy, G., Lambert, J., Van Dorsselaer, A., Hoffmann, J. A., and Hetru, C. (1995) Biochemistry 34, 7394-400.
6. Bulet, P., Dimarcq, J. L., Hetru, C., Lagueux, M., Charlet, M., Hegy, G., Van Dorsselaer, A., and Hoffmann, J. A. (1993) J. Biol. Chem. 268, 14893-7.
7. Hara, S., and Yamakawa, M. (1995) Biochem. J. 310, 651-6.
8. Bulet, P. (1999) Medicine/Sciences 15, 23-9.
9. Engström, P., Carlsson, A., Engström, A., Tao, Z.-j., and Bennich, H. (1984) EMBO J. 3, 3347-51.
10. Carlsson, A., Engström, P., Palva, E. T., and Bennich, H. (1991) Infect. Immun. 59, 3040-5.
11. Carlsson, A., Nystrom, T., de Cock, H., and Bennich, H. (1998) Microbiol. 144, 2179-88.
12. Casteels, P., and Tempst, P. (1994) Biochem. Biophys. Res. Commun. 199, 339-45.
13. Bulet, P., Urge, L., Ohresser, S., Hetru, C., and Otvos, L., Jr. (1996) Eur. J. Biochem. 238, 64-9.
14. Keppi, E., Pugsley, A. P., Lambert, J., Wicker, C., Dimarcq, J., Hoffmann, J. A., and Hoffmann, D. (1989) Arch. Insect Biochem. Physiol. 10, 229-239.
15. Kuduk, S. D., Schwarz, J. B., Chen, X. T., Glunz, P. W., Sames, D., Ragupathi, G., Livingston, P. O., and Danishefsky, S. J. (1998) J. Am. Chem. Soc. 120, 12474-12485.
16. Sames, D., Chen, X. T., and Danishefsky, S. J. (1997) Nature 389, 587-91.
17. Klich, G., Paulsen, H., Meyer, B., Meldal, M., and Bock, K. (1997) Carbohydr. Res. 299, 33-48.
18. Andreotti, A. H., and Kahne, D. (1993) J. Am. Chem. Soc. 115, 3352-3353.
19. Paulsen, H., and Adermann, K. (1989) Liebigs Ann. Chem., 751-769.
20. Szabó, L., Ramza, J., Langdon, C., and Polt, R. (1995) Carbohydr. Res. 274, 11-28.
21. Shull, B. K., Wu, Z. J., and Koreeda, M. (1996) J. Carbohydr. Chem. 15, 955-964.
22. Shafizadeh, F. (1963) Methods Carbohydr. Chem. 2, 409-410.
23. Barnett, J. E. (1967) Adv. Carbohydr. Chem. Biochem. 22, 177-227.
24. Higashi, K., Nakayama, K., Shioya, E., and Kusama, T. (1991) Chem. Pharm. Bull. 39, 2502-2504.
25. Lemieux, R. U., and Ratcliffe, R. M. (1979) Can. J. Chem. 57, 1244-1251.
26. Kunz, H., Birnbach, S., and Wernig, P. (1990) Carbohydr. Res. 202, 207-223.
27. Chang, C. D., Waki, M., Ahmad, M., Meienhofer, J., Lundell, E. O., and Haug, J. D. (1980) Int. J. Peptide Prot. Res. 15, 59-66.
28. King, D. S., Fields, C. G., and Fields, G. B. (1990) Int. J. Peptide Prot. Res. 36, 255-66.
29. Pace, C. N., Vajdos, F., Fee, L., Grimsley, G., and Gray, T. (1995) Protein Sci. 4, 2411-23.
30. Falla, T. J., and Hancock, R. E. W. (1997) Antimicrob. Agents Chemother. 41, 771-5.
31. Satyanarayana, J., Gururaja, T. L., Naganagowda, G. A., Ramasubbu, N., and Levine, M. J. (1998) J. Peptide Res. 52, 165-79.
32. Kunz, H. (1996) in Preparative Carbohydrate Chemistry (Hanessian, S., Ed.) pp 265-281, Marcel Dekker, Inc., New York.
33. Yang, Y., Sweeney, W. V., Schneider, K., Thörnqvist, S., Chait, B. T., and Tam, J. P. (1994) Tetrahedron Lett. 35, 9689-9692.
34. Quibell, M., Owen, D., Packman, L. C., and Johnson, T. (1994) J. Chem. Soc., Chem. Commun., 2343-2344.
35. Packman, L. C. (1995) Tetrahedron Lett. 36, 7523-7526.
36. Woody, R. W. (1996) in Circular dichroism and the conformational analysis of biomolecules (Fasman, G. D., Ed.) pp 25-67, Plenum, New York.
37. O'Neil, K. T., and DeGrado, W. F. (1990) Science 250, 646-51.
38. Kim, C. A., and Berg, J. M. (1993) Nature 362, 267-70.
39. Gunne, H., Hellers, M., and Steiner, H. (1990) Eur. J. Biochem. 187, 699-703.
40. McManus, A. M., Otvos, L., Jr., Hoffmann, R., and Craik, D. J. (1999) Biochemistry 38, 705-14.
41. Hancock, R. E., and Wong, P. G. (1984) Antimicrob. Agents Chemother. 26, 48-52.
42. Hancock, R. E. (1984) Annu. Rev. Microbiol. 38, 237-64.
43. Nikaido, H., and Vaara, M. (1985) Microbiol. Rev. 49, 1-32.
44. Hancock, R. E. W. (1987) J. Bacteriol. 169, 929-33.
45. Boman, H. G., Agerberth, B., and Boman, A. (1993) Infect. Immun. 61, 2978-84.
46. Wade, D., Boman, A., Wahlin, B., Drain, C. M., Andreu, D., Boman, H. G., and Merrifield, R. B. (1990) Proc. Natl. Acad. Sci. U.S.A. 87, 4761-5.
47. Mancheño, J. M., Oñaderra, M., Martínez del Pozo, A., Díaz-Achirica, P., Andreu, D., Rivas, L., and Gavilanes, J. G. (1996) Biochemistry 35, 9892-9.
48. Ishikawa, M., Kubo, T., and Natori, S. (1992) Biochem. J. 287, 573-8.
49. Wicker, C., Reichhart, J. M., Hoffmann, D., Hultmark, D., Samakovlis, C., and Hoffmann, J. A. (1990) J. Biol. Chem. 265, 22493-8.
50. Mackintosh, J. A., Veal, D. A., Beattie, A. J., and Gooley, A. A. (1998) J. Biol. Chem. 273, 6139-43.
51. Lee, J. Y., Boman, A., Sun, C. X., Andersson, M., Jörnvall, H., Mutt, V., and Boman, H. G. (1989) Proc. Natl. Acad. Sci. U.S.A. 86, 9159-62.
52. Callaway, J. E., Lai, J., Haselbeck, B., Baltaian, M., Bonnesen, S. P., Weickmann, J., Wilcox, G., and Lei, S. P. (1993) Antimicrob. Agents Chemother. 37, 1614-9.
53. Cumming, D. A. (1991) Glycobiol. 1, 115-30.
54. Engström, Å., Engström, P., Tao, Z.-j., Carlsson, A., and Bennich, H. (1984) EMBO J. 3, 2065-2070.
55. Kockum, K., Faye, I., von Hofsten, P., Lee, J.-Y., Xanthopoulos, K. G., and Boman, H. G. (1984) EMBO J. 3, 2071-2075.
56. Ando, K., Okada, M., and Natori, S. (1987) Biochemistry 26, 226-30.
57. Cociancich, S., Dupont, A., Hegy, G., Lanot, R., Holder, F., Hetru, C., Hoffmann, J. A., and Bulet, P. (1994) Biochem. J. 300, 567-75.
58. Casteels, P., Ampe, C., Jacobs, F., Vaeck, M., and Tempst, P. (1989) EMBO J. 8, 2387-91.