Controlling the Substrate Selectivity of Deacetoxycephalosporin/deacetylcephalosporin C Synthase

Journal of Biological Chemistry

Volumn 279, Issue 15, 2004, Pages 15420-15426

  Lloyd, Matthew D ^a   Lipscomb, Sarah J ^b   Hewitson, Kirsty S ^b   Hensgens, Charles M H ^b   Baldwin, Jack E ^b   Schofield, Christopher J ^b  

^a University of Bath   (United Kingdom)

^b UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHESIS; CATALYSIS; ENZYME KINETICS; MUTAGENESIS; REACTION KINETICS; SUBSTRATES;

MUTATION; OXIDATIVE REACTIONS;

BIOCHEMISTRY;

2 OXOGLUTARIC ACID; ADICILLIN; ASPARAGINE; DEACETOXYCEPHALOSPORIN C; DEACETOXYCEPHALOSPORIN C SYNTHASE; DEACETYLCEPHALOSPORIN C; DEACETYLCEPHALOSPORIN C SYNTHASE; MUTANT PROTEIN; OXOGLUTARATE DEHYDROGENASE; SYNTHETASE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANIMAL CELL; ARTICLE; CARBOXY TERMINAL SEQUENCE; CATALYSIS; CONTROLLED STUDY; ENZYME ACTIVE SITE; ENZYME SPECIFICITY; ENZYME SUBSTRATE; ENZYME SYNTHESIS; HYDROXYLATION; NONHUMAN; NUCLEOTIDE SEQUENCE; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; PROTEIN MODIFICATION; SITE DIRECTED MUTAGENESIS; WILD TYPE;

ACREMONIUM; AMINO ACID SEQUENCE; ASPARAGINE; BINDING SITES; CEPHALOSPORINS; CLONING, MOLECULAR; INTRAMOLECULAR TRANSFERASES; IRON; KINETICS; METHIONINE; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MUTAGENESIS, SITE-DIRECTED; MUTATION; OXYGEN; OXYGENASES; PENICILLIN-BINDING PROTEINS; PENICILLINS; POINT MUTATION; PROTEIN BINDING; PROTEIN STRUCTURE, TERTIARY; SEQUENCE HOMOLOGY, AMINO ACID; STREPTOMYCES; SUBSTRATE SPECIFICITY; TRYPTOPHAN;

ACREMONIUM CHRYSOGENUM; ANIMALIA; CEPHALOSPORIUM; STREPTOMYCES; STREPTOMYCES CLAVULIGERUS;

EID: 2442622564     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.M313928200     Document Type: Article

References (43)

1. Baldwin, J. E., Adlington, R. M., Coates, J. B., Crabbe, M. J. C., Crouch, N. P., Keeping, J. W., Knight, G. C., Schofield, C. J., Ting, H. H., Vallejo, C. A., Thorniley, M., and Abraham, E. P. (1987) Biochem. J. 245, 831-841
2. Scheidegger, A., Kuenzi, M. T., and Nuesch, J. (1984) J. Antibiotics 37, 522-531
3. Prescott, A. G., and Lloyd, M. D. (2000) Nat. Prod. Rep. 17, 367-383
4. Prescott, A. G. (1993) J. Exp. Bot. 44, 849-861
5. Ryle, M. J., and Hausinger, R. P. (2002) Curr. Opin. Chem. Biol. 6, 193-201
6. Kovacevic, S., Weigal, B. J., Tobin, M. B., Ingolia, T., and Miller, J. R. (1989) J. Bacteriol. 171, 754-760
7. Lloyd, M. D., Lee, H.-J., Harlos, K., Zhang, Z. H., Baldwin, J. E., Schofield, C. J., Charnock, J. M., Garner, C. D., Hara, T., Terwisscha van Scheltinga, A. C., Valegård, K., Viklund, J. A. C., Hajdu, J., Andersson, I., Danielsson, Å., and Bhikhabhai, R. (1999) J. Mol. Biol. 287, 943-960
8. Kovacevic, S., and Miller, J. R. (1991) J. Bacteriol. 173, 398-400
9. Valegård, K., Terwisscha van Scheltinga, A. C., Lloyd, M. D., Hara, T., Ramaswamy, S., Perrakis, A., Thompson, A., Lee, H.-J., Baldwin, J. E., Schofield, C. J., Hajdu, J., and Andersson, I. (1998) Nature 394, 805-809
10. Lee, H.-J., Lloyd, M. D., Clifton, I. J., Harlos, K., Dubus, A., Baldwin, J. E., Frere, J.-M., and Schofield, C. J. (2001) J. Biol. Chem. 276, 18290-18295
11. Lee, H.-J., Lloyd, M. D., Harlos, K., Clifton, I. J., Baldwin, J. E., and Schofield, C. J. (2001) J. Mol. Biol. 308, 937-948
12. Lee, H.-J., Lloyd, M. D., Harlos, K., and Schofield, C. J. (2000) Biochem. Biophys. Res. Commun. 267, 445-448
13. Lee, H.-J., Schofield, C. J., and Lloyd, M. D. (2002) Biochem. Biophys. Res. Commun. 292, 66-70
14. Lee, H.-J., Dai, Y.-F., Shiau, C.-Y., Schofield, C. J., and Lloyd, M. D. (2003) Eur. J. Biochem. 270, 1301-1307
15. Lipscomb, S. J., Lee, H.-J., Mukherji, M., Baldwin, J. E., Schofield, C. J., and Lloyd, M. D. (2002) Eur. J. Biochem. 269, 2735-2739
16. Townsend, C. A., Theis, A. B., Neese, A. S., Barrabee, E. B., and Poland, D. (1985) J. Am. Chem. Soc. 107, 4760-4767
17. Baldwin, J. E., Adlington, R. M., Crouch, N. P., Turner, N. J., and Schofield, C. J. (1989) J. Chem. Soc. Chem. Commun. 1141-1143
18. Townsend, C. A., and Barrabee, E. B. (1984) J. Chem. Soc. Chem. Commun. 1586-1588
19. Baldwin, J. E., Adlington, R. M., Aplin, R. T., Crouch, N. P., and Wilkinson, R. (1992) Tetrahedron 48, 6853-6862
20. Baldwin, J. E., Adlington, R. M., Crouch, N. P., and Pereira, I. A. C. (1993) Tetrahedron 49, 7499-7518
21. Baldwin, J. E., Goh, K.-C., Wood, M. E., Schofield, C. J., Cooper, R. D. G., and Huffman, G. W. (1991) Bioorg. Med. Chem. Lett. 1, 421-424
22. Baldwin, J. E., Blackburn, J. M., Heath, R. J., and Sutherland, J. D. (1992) Bioorg. Med. Chem. Lett. 2, 663-668
23. Sambrook, J., Fritsch, E. F., and Maniatis, T. (1989) Molecular Cloning: A Laboratory Manual, 2nd Ed., Cold Spring Harbor Laboratory, Cold Spring Harbor, NY
24. Jones, T. A., Zou, J.-Y., Cowan, S. W., and Kjeldgaard, M. (1991) Acta Crystallogr. Sect. A 47, 110-119
25. Rost, B., and Sander, C. (1993) J. Mol. Biol. 232, 584-599
26. Bradford, M. M. (1976) Anal. Biochem. 72, 248-254
27. Dubus, A., Lloyd, M. D., Lee, H.-J., Schofield, C. J., Baldwin, J. E., and Frere, J.-M. (2001) Cell. Mol. Life Sci. 58, 835-843
28. Shibata, N., Lloyd, M. D., Baldwin, J. E., and Schofield, C. J. (1996) Bioorg. Med. Chem. Lett. 6, 1579-1584
29. Baldwin, J. E., Adlington, R. M., Crabbe, M. J., Knight, G. C., Nomoto, T., Schofield, C. J., and Ting, H.-H. (1987) Tetrahedron 43, 3009-3014
30. Baldwin, J. E., Adlington, R. M., Coates, J. B., Crabbe, M. J. C., Keeping, J. W., Knight, G. C., Nomoto, T., Schofield, C. J., and Ting, H.-H. (1987) J. Chem. Soc. Chem. Commun. 374-375
31. Hamilton, C. S., Yasuhara, A., Baldwin, J. E., Lloyd, M. D., and Rutledge, P. J. (2001) Bioorg. Med. Chem. Lett. 11, 2511-2514
32. Chin, H. S., Sim, J., and Sim, T. S. (2001) Biochem. Biophys. Res. Commun. 287, 507-513
33. Chin, H.-S., Sim, J., Seah, I., and Sim, T. S. (2003) FEMS Microbiol. Lett. 218, 251-257
34. Price, J. C., Barr, E. W., Glass, T. E., Krebs, C., and Bollinger, J. M. (2003) J. Am. Chem. Soc. 125, 13008-13009
35. Price, J. C., Barr, E. W., Tirupati, B., Bollinger, J. M., and Krebs, C. (2003) Biochemistry 47, 7497-7508
36. Zhou, J., Gunsior, M., Bachmann, B., Townsend, C. A., and Soloman, E. I. (1998) J. Am. Chem. Soc. 120, 13539-13540
37. Pavel, E. G., Zhou, L., Busby, R. W., Gunsior, M., Townsend, C. A., and Soloman, E. I. (1998) J. Am. Chem. Soc. 120, 743-753
38. Schofield, C. J., and Zhang, Z.-H. (1999) Curr. Opin. Struct. Biol. 9, 722-731
39. Wei, C.-L., Yang, Y. B., Wang, W.-C., Liu, W.-C., Hsu, J.-H., and Tsai, Y.-C. (2003) Appl. Microbiol. Biotech. 69, 2306-2312
40. Aharonowitz, Y., Cohen, G., and Martin, J. F. (1992) Annu. Rev. Microbiol. 46, 461-495
41. Lloyd, M. D., Merritt, K. D., Lee, V., Sewell, T. J., Wha-Son, B., Baldwin, J. E., Schofield, C. J., Elson, S. W., Baggaley, K. H., and Nicholson, N. H. (1999) Tetrahedron 55, 10201-10220
42. Hedden, P., and Phillips, A. L. (2000) Trends Plant Sci. 5, 523-530
43. Broun, P., Shanklin, J., Whittle, E., and Somerville, C. (1998) Science 282, 1315-1317