Mechanism of action and identification of Asp242 as the catalytic nucleophile of Vibrio furnisii N-acetyl-β-D-glucosaminidase using 2- acetamido-2-deoxy-5-fluoro-α-L-idopyranosyl fluoride

Biochemistry

Volumn 39, Issue 1, 2000, Pages 117-126

  Vocadlo, David J ^a   Mayer, Christoph ^a   He, Shouming ^a   Withers, Stephen G ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ASPARTIC ACID; N (2 FLUORENYL)ACETAMIDE; N ACETYL BETA GLUCOSAMINIDASE; PYRANOSIDE; REAGENT;

AMINO ACID SEQUENCE; ARTICLE; CATALYSIS; ENZYME ACTIVE SITE; ENZYME MECHANISM; ENZYME SUBSTRATE; HYDROLYSIS; MASS SPECTROMETRY; MICHAELIS MENTEN KINETICS; NONHUMAN; PRIORITY JOURNAL; VIBRIO FURNISSII;

ACETYLGLUCOSAMINIDASE; ASPARTIC ACID; BINDING SITES; CATALYSIS; HYDROLYSIS; INDICATORS AND REAGENTS; KINETICS; MONOSACCHARIDES; PEPTIDES; SEQUENCE ALIGNMENT; SEQUENCE ANALYSIS, PROTEIN; SEQUENCE HOMOLOGY, AMINO ACID; STRUCTURE-ACTIVITY RELATIONSHIP; VIBRIO;

EID: 0034635169     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi991958d     Document Type: Article

References (49)

1. Mahuran, D. J. (1991) Biochim. Biophys. Acta 1096, 87-94.
2. Scigelova, M., and Crout, D. H. G. (1999) Enzymol. Microb. Technol. 25, 3-14.
3. Morsch, M., Mayer, C., Sennhauser, U., and Rast, D. M. (1997) Phamacol. Ther. 76, 187-218.
4. Tsujibo, H., Hatano, N., Mikama, T., Hirasawa, A., Miyamoto, K., and Inamori, Y. (1998) Appl. Environ. Microbiol. 64, 2920-2924.
5. Henrissat, B., and Bairoch, A. (1996) Biochem. J. 316, 695-696.
6. Chitlaru, E., and Roseman, S. (1996) J. Biol. Chem. 271, 33433-33439.
7. Legler, G., Sinnott, M. L., and Withers, S. G. (1980) J. Chem. Soc., Perkins Trans. 2, 1376-1388.
8. Hrmova, M., and Fincher, G. B. (1998) Carbohydr. Res. 305, 209-221.
9. Hrmova, M., Harvey, A. J., Wang, J., Shirley, N. J., Jones, G. P., Stone. B. A., Høj, P. B., and Fincher, G. B. (1996) J. Biol. Chem. 271, 5277-5286.
10. Legler, G., Roeser, K.-R., and Illig, H.-K. (1979) Eur. J. Biochem. 101, 85-92.
11. Davies, G., Sinnott, M. L., and Withers, S. G. (1998) in Comprehensive Biological Catalysis, pp 119-208, Academic Press, London.
12. Varghese, J. N., Hrmova, M., and Fincher, G. B. (1999) Structure 7, 179-190.
13. Bause, E., and Legler, G. (1980) Biochim. Biophys. Acta 626, 459-465.
14. Gebler, J. C., Aebersold, R., and Withers, S. G. (1992) J. Biol. Chem. 267, 11126-11130.
15. He, S., and Withers, S. G. (1997) J. Biol. Chem. 272, 24864-24867.
16. Tews, I., Perrakis, A., Oppenheim, A., Dauter, Z., Wilson, K. S., and Vorgias, C. E. (1996) Nat. Stuct. Biol. 3, 638-648.
17. Knapp, S., Vocadlo, D., Gao, Z., Kirk, B., Lou, J., and Withers, S. G. (1996) J. Am. Chem. Soc. 118, 6804-6805.
18. Drouillard, S., Armand, S., Davies, G. J., Vorgias, C. E., and Henrissat, B. (1997) Biochem. J. 328, 945-949.
19. Legler, G., and Bollhagen, R. (1992) Carbohydr. Res. 233, 113-123.
20. Kobayashi, S., Kiyosada, T., and Shoda, S.-I. (1997) Tetrahedron Lett. 38, 2111-2112.
21. Matsumura, I., and Kirsch, J. F. (1996) Biochemistry 35, 1881-1889.
22. Hashimoto, Y., Yamada, K., Motoshima, H., Omura, T., Yamada, H., Yasukochi, T., Miki, T., Ueda, T., and Imoto, T. (1996) J. Biochem. 119, 145-150.
23. Vocadlo, D. J., MacKenzie, L. F., He, S., Zeikus, G. J., and Withers, S. G. (1998) Biochem. J. 335, 449-455.
24. Wong, A. W., He, S., Grubb, J. H., Sly, W. S., and Withers, S. G. (1998) J. Biol. Chem. 273, 34057-34062.
25. Miao, S. C., Ziser, L., Aebersold, R., and Withers, S. G. (1994) Biochemistry 33, 7027-7032.
26. Howard, S., He, S., and Withers, S. G. (1998) J. Biol. Chem. 273, 2067-2072.
27. McCarter, J. D., and Withers, S. G. (1996) J. Am. Chem. Soc. 118, 241-242.
28. McCarter, J. D., and Withers, S. G. (1996) J. Biol. Chem. 271, 6889-6894.
29. Withers, S. G., and Aebersold, R. (1995) Protein Sci. 4, 361-372.
30. Ballardie, F. W., Capon, B., Dearie, W. M., and Foster, R. L. (1976) Carbohydr. Res. 49, 79-92.
31. Leatherbarrow, R. J. (1992) Erithacus Software Ltd., Staines, U.K.
32. Praly, J.-P., Brard, L., Descotes, G., and Toupet, L. (1989) Tetrahedron 45, 4141-4152.
33. Altschul, S. F., Gish, W., Miller, W., Myers, E. W., and Lipman, D. J. (1990) J. Mol. Biol. 215, 403-410.
34. Thompson, J. D., Higgins, D. G., and Gibson, T. J. (1994) Nucleic Acids Res. 22, 4673-4680.
35. Blattner, F. R., Plunkett, G. I., Bloch, C. A., Perna, N. T., Burland, V., Riley, M., Collada-Vides, J., Glasner, F. D., Rode, C. K., Mayhew, G. F., Gregor, J., Davis, N. W., Kirkpatrick, H. A., Goeden, M. A., Rose, D. J., Mau, B., and Shao, Y. (1997) Science 277, 1453-1474.
36. Fleischmann, R. D., Adams, M. D., White, O., Clayton, R. A., Kirkness, E. F., Kerlavage, A. R., Bult, C. J., Tomb, J., Dougherty, B. A., Merrick, J. M., McKenney, K., Sutton, G. G., FitzHugh, W., Fields, C. A., Gocayne, J. D., Scott, J. D., Shirley, R., Liu, L. I., Glodek, A., Kelley, J. M., Weidman, J. F., Phillips, C. A., Spriggs, T., Hedblom, E., Cotton, M. D., Utterback, T., Hanna, M. C., Nguyen, D. T., Saudek, D. M., Brandon, R. C., Fine, L. D., Fritchman, J. L., Fuhrmann, J. L.. Geoghagen, N. S., Gnehm, C. L., McDonald, L. A., Small, K. V., Fraser, C. M., Smith, H. O., and Venter, J. C. (1995) Science 269, 496-512.
37. Cole, S. T., Brosch, R., Parkhill, J., Gamier, T., Churcher, C., Harris, D., Gordon, S. V., Eiglmeier, K., Gas, S., Barry, C. E., III, Tekaia, F., Badcock, K., Basham, D., Brown, D., Chillingworth, T., Connor, R., Davies, R., Devlin, K., Feltwell, T., Gentles, S., Hamlin, N., Holroyd, S., Hornsby, T., Jagels, K., Krogh, A., McLean, J., Moule, S., Murphy, L., Oliver, S., Osborne, J., Quail, M. A., Rajandream, M. A., Rogers, J., Rutter, S., Seeger, K., Skelton, S., Squares, S., Sqares, R., Sulston, J. E., Taylor, K., Whitehead, S., and Barrell, B. G. (1998) Nature 393, 537-544.
38. Eiglmeier, K., Honore, N., Woods, S. A., Caudron, B., and Cole, S. T. (1993) Mol. Microbiol. 7, 197-206.
39. Andersson, S. G., Zomorodipour, A., Andersson, J. O., Sicheritz-Ponten, T., Alsmark, U. C., Podowski, R. M., Naslund, A. K., Eriksson, A. S., Winkler, H. H., and Kurland, C. G. (1998) Nature 396, 133-140.
40. Lee, H. J., and Kang, H. S. (1999) GenBank electronic submission, Sequence analysis of 43D2 fosmid clone of Zvmomonas mobilis ZM4; Accession Number AF124757.1.
41. Quirk, P. G., Guffanti, A. A., Clejan, S., Cheng, J., and Krulwich, T. A. (1994) Biochim. Biophys. Acta 1186(1-2), 27-34.
42. Tsujibo, H., Fujimoto, K., Tanno, H., Miyamoto, K., Imada, C., Okami, Y., and Inamori, Y. (1994) Gene 146, 111-115.
43. Redenbach, M., Kieser, H. M., Denapaite, D., Eichner, A., Cullum, J., Kinashi, H., and Hopwood, D. A. (1996) Mol. Microbiol. 21(1), 77-96.
44. Kaneko, T., Sato, S., Kotani, H., Tanaka, A., Asamizu, E., Nakamura, Y., Miyajima, N., Hirosawa, M., Sugiura, M., Sasamoto, S., Kimura, T., Hosouchi, T., Matsuno, A., Muraki, A., Nakazaki, N., Naruo, K., Okumura, S., Shimpo, S., Takeuchi, C., Wada, T., Watanabe, A., Yamada, M., Yasuda, M., and Tabata, S. (1996) DNA Res. 3, 109-136.
45. Nelson, K. E., Clayton, R. A., Gill, S. R., Gwinn, M. L., Dodson, R. J., Haft, D. H., Hickey, E. K., Peterson, J. D., Nelson, W. C., Ketchum, K. A., McDonald, L., Utterback, T. R., Malek, J. A., Linher, K. D., Garrett, M. M., Stewart, A. M., Cotton, M. D., Pratt, M. S., Phillips, C. A., Richardson, D., Heidelberg, J., Sutton, G. G., Fleischmann, R. D., White, O., Salzberg, S. L., Smith, H. O., Venter, J. C., and Fraser, C. M. (1999) Nature 399, 323-329.
46. Fraser, C. M., Casjens, S., Huang, W. M., Sutton, G. G., Clayton, R. A., Lathigra, R., White, O., Ketchum, K. A., Dodson, R., Hickey, E. K., Gwinn, M., Dougherty, B., Tomb, J.-F., Fleischmann, R. D., Richardson, D., Peterson, J., Kerlavage, A. R., Quackenbush, J., Salzberg, S., Hanson, M., van-Vugt, R., Palmer, N., Adams, M. D., Gocayne, J. D., Weidman, J., Utterback, T., Watthey, L., McDonald, L., Artiach, P., Bowman, C., Garland, S., Fujii, C., Cotton, M. D., Horst, K., Roberts, K., Hatch, B., Smith, H. O., and Venter, J. C. (1997) Nature 390, 580-586.
47. Castle, L. A., Smith, K. D., and Morris, R. O. (1992) J. Bacteriol. 174, 1478-1486.
48. Grabnitz, F., Rucknagel, K. P., Seiss, M., and Staudenbauer, W. L. (1989) Mol. Gen. Genet. 217, 70-76.
49. Kawaguchi, T., Enoki, T., Tsurumaki, S., Sumitani, J., Ueda, M., Ooi, T., and Arai, M. (1996) Gene 173, 287-288.