Structural and mechanistic studies on carboxymethylproline synthase (CarB), a unique member of the crotonase superfamily catalyzing the first step in carbapenem biosynthesis

Journal of Biological Chemistry

Volumn 280, Issue 41, 2005, Pages 34956-34965

  Sleeman, Mark C ^a   Sorensen, John L ^a   Batchelar, Edward T ^a   McDonough, Michael A ^a   Schofield, Christopher J ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTICS; BIOSYNTHESIS; CONFORMATIONS; ESTERS; HYDROLYSIS; ISOTOPES; MEDICAL IMAGING; MUTAGENESIS; PROBABILITY;

CONFORMATIONAL CHANGES; CYCLIZATION; SIDE CHAIN; STRUCTURAL WORK;

ENZYMES;

3 HYDROXYISOBUTYRYL COENZYME A HYDROXYLASE; ACYL COENZYME A; ALDEHYDE; BETA LACTAM ANTIBIOTIC; CARBAPENEM DERIVATIVE; CARBOXYMETHYLPROLINE; CARBOXYMETHYLPROLINE SYNTHASE; ENOYL COENZYME A HYDRATASE; GLUTAMIC ACID; HISTIDINE; MALONYL COENZYME A; OXYGENASE; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ANTIBIOTIC BIOSYNTHESIS; ARTICLE; CATALYSIS; CONFORMATIONAL TRANSITION; CYCLIZATION; DECARBOXYLATION; ENZYME MECHANISM; ENZYME SPECIFICITY; ENZYME STRUCTURE; HYDROLYSIS; MUTAGENESIS; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

ALDEHYDES; ANHYDRIDES; BINDING SITES; CARBAPENEMS; CARBON-CARBON LYASES; CATALYSIS; CHROMATOGRAPHY, LIQUID; CRYSTALLOGRAPHY, X-RAY; ENOYL-COA HYDRATASE; ESCHERICHIA COLI; ESTERS; GLUTAMATES; GLUTAMIC ACID; HISTIDINE; HYDROGEN BONDING; MASS SPECTROMETRY; MODELS, CHEMICAL; MODELS, MOLECULAR; MUTAGENESIS; PROLINE; PROTEIN BINDING; PROTEIN CONFORMATION; PROTEIN STRUCTURE, SECONDARY; SELENOMETHIONINE; SUBSTRATE SPECIFICITY; THIOLESTER HYDROLASES; TRYPSIN;

EID: 27144549032     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.M507196200     Document Type: Article

References (52)

1. Page, M. I. (1992) The Chemistry of β-Lactams, pp. 1-78, Blackie Academic and Professional, London, UK
2. Schofield, C. J., Baldwin, J. E., Byford, M. F., Clifton, I., Hajdu, J., Hensgens, C., and Roach, P. (1997) Curr. Opin. Struct. Biol. 7, 857-864
3. Baggaley, K. H., Brown, A. G., and Schofield, C. J. (1997) Nat. Prod. Rep. 14, 309-333
4. Jensen, S. E., and Paradkar, A. S. (1999) Antonie Van Leeuwenhoek 75, 125-133
5. Townsend, C. A. (2002) Curr. Opin. Chem. Biol. 6, 583-589
6. Bachmann, B. O., Li, R., and Townsend, C. A. (1998) Proc. Natl. Acad. Sci. U. S. A. 95, 9082-9086
7. Gerratana, B., Stapon, A., and Townsend, C. A. (2003) Biochemistry 42, 7836-7847
8. McNaughton, H. J., Thirkettle, J. E., Zhang, Z., Schofield, C. J., Jensen, S. E., Barton, B., and Greaves, P. (1998) Chem. Commun. 2325-2326
9. McGowan, S. J., Sebaihia, M., Porter, L. E., Stewart, G. S. A. B., Williams, P., Bycroft, B. W., and Salmond, G. P. C. (1996) Mol. Microbiol. 22, 415-426
10. Hodgson, J. E., Fosberry, A. P., Rawlinson, N. S., Ross, H. N. M., Neal, R. J., Arnell, J. C., Earl, A. J., and Lawlor, E. J. (1995) Gene (Amst.) 166, 49-55
11. Jensen, S. E., Elder, K. J., Aidoo, K. A., and Paradkar, A. S. (2000) Antimicrob. Agents Chemother. 44, 720-726
12. Khaleeli, N., Li, R., and Townsend, C. A. (1999) J. Am. Chem. Soc. 121, 9223-9224
13. Li, R., Stapon, A., Blanchfield, J. T., and Townsend, C. A. (2000) J. Am. Chem. Soc. 122, 9296-9297
14. Sleeman, M. C., and Schofield, C. J. (2004) J. Biol. Chem. 279, 6730-6736
15. Gerratana, B., Arnett, S. O., Stapon, A., and Townsend, C. A. (2004) Biochemistry 43, 15936-15945
16. Mursula, A. M., Hiltunen, J. K., and Wierenga, R. K. (2004) FEBS Lett. 557, 81-87
17. Holden, H. M., Benning, M. M., Haller, T., and Gerlt, J. A. (2001) Acc. Chem. Res. 34, 145-157
18. Wong, B. J., and Gerlt, J. A. (2003) J. Am. Chem. Soc. 125, 12076-12077
19. Walter, T. S., Diprose, J. M., Mayo, C. J., Siebold, C., Pickford, M. G., Carter, L., Sutton, G. C., Berrow, N. S., Brown, J., Berry, I. M., Stewart-Jones, G. B. E., Grimes, J. M., Stammers, D. K., Esnouf, R. M., Jones, E. Y., Owens, R. J., Stuart, D. I., and Harlos, K. (2005) Acta Crystallogr. D. Biol. Crystallogr. 61, 651-657
20. Leslie, A. G. W. (1992) Joint CCP4 + ESF-EAMCB Newsletter on Protein Crystallography, Daresbury Laboratory, Warrington, UK
21. Collaborative (1994) Acta Crystallogr. D. Biol. Crystallogr. 50, 760-763
22. Cianci, M., Antonyuk, S., Bliss, N., Bailey, M. W., Buffey, S. G., Cheung, K. C., Clarke, J. A., Derbyshire, G. E., Ellis, M. J., Enderby, M. J., Grant, A. F., Holbourn, M. P., Laundy, D., Nave, C., Ryder, R., Stephenson, P., Helliwell, J. R., and Hasnain, S. S. (2005) J. Synchrotron Radiat. 12, 455-466
23. Otwinowski, Z., and Minor, W. (1997) Methods Enzymol. 276, 307-326
24. Sheldrick, G. M., and Schneider, T. R. (1997) Methods Enzymol. 277, 319-343
25. Bruker (2003) XPREP-Data Preparation and Reciprocal Space Exploration, Ver. 6.14, Bruker AXS Inc., Madison, WI
26. Terwilliger, T. (2000) Acta Crystallogr. D. Biol. Crystallogr. 56, 965-972
27. Emsley, P., and Cowtan, K. (2004) Acta Crystallogr. D. Biol. Crystallogr. 60, 2126-2132
28. Murshudov, G. N., Vagin, A. A., and Dodson, E. J. (1997) Acta Crystallogr. D. Biol. Crystallogr. 53, 240-255
29. McCoy, A. J., Grosse-Kunstleve, R. W., Storoni, L. C., and Read, R. J. (2005) Acta Crystallogr. D. Biol. Crystallogr. 61, 458-464
30. Storoni, L. C., McCoy, A. J., and Read, R. J. (2004) Acta Crystallogr. D. Biol. Crystallogr. 60, 432-438
31. Verdonk, M. L., Cole, J. C., Hartshorn, M. J., Murray, C. W., and Taylor, R. D. (2003) Proteins 52, 609-623
32. Krissinel, E., and Henrick, K. (2004) Acta Crystallogr. D. Biol. Crystallogr. 60, 2256-2268
33. Collado, I., Ezquerra, J., Vaquero, J. J., and Pedregal, C. (1994) Tetrahedron Lett. 35, 8037-8040
34. Sorensen, J. L., Sleeman, M. C., and Schofield, C. J. (2005) Chem. Commun. 1155-1157
35. Benning, M. M., Taylor, K. L., Liu, R. Q., Yang, G., Xiang, H., Wesenberg, G., Dunaway-Mariano, D., and Holden, H. M. (1996) Biochemistry 35, 8103-8109
36. Modis, Y., Filppula, S. A., Novikov, D. K., Norledge, B., Hiltunen, J. K., and Wierenga, R. K. (1998) Structure 6, 957-970
37. Laskowski, R. A., MacArthur, M. W., Moss, D. S., and Thornton, J. M. (1993) J. Appl. Crystallogr. 26, 283-291
38. Kleywegt, G. J., and Jones, T. A. (1994) Acta Crystallogr. D. Biol. Crystallogr. 50, 178-185
39. Engel, C. K., Mathieu, M., Zeelen, J. P., Hiltunen, J. K., and Wierenga, R. K. (1996) EMBO J. 15, 5135-5145
40. Kurimoto, K., Fukai, S., Nureki, O., Muto, Y., and Yokoyama, S. (2001) Structure 9, 1253-1263
41. Mursula, A. M., van Aalten, D. M. F., Hiltunen, J. K., and Wierenga, R. K. (2001) J. Mol. Biol. 309, 845-853
42. Benning, M. M., Haller, T., Gerlt, J. A., and Holden, H. M. (2000) Biochemistry 39, 4630-4639
43. Whittingham, J. L., Turkenburg, J. P., Verma, C. S., Walsh, M. A., and Grogan, G. (2003) J. Biol. Chem. 278, 1744-1750
44. Truglio, J. J., Theis, K., Feng, Y., Gajda, R., Machutta, C., Tonge, P. J., and Kisker, C. (2003) J. Biol. Chem. 278, 42352-42360
45. Engel, C. K., Kiema, T. R., Hiltunen, J. K., and Wierenga, R. K. (1998) J. Mol. Biol. 275, 847-859
46. Sleeman, M. C., Smith, P., Kellam, B., Chhabra, S. R., Bycroft, B. W., and Schofield, C. J. (2004) Chembiochem. 5, 879-882
47. Carreras, C. W., Pieper, R., and Khosla, C. (1997) in The Chemistry and Biology of Fatty Acid, Polyketide, and Nonribosomal Peptide Biosynthesis, Vol. 188, pp. 85-126, Springer-Verlag, Berlin
48. McDaniel, R., Welch, M., and Hutchinson, C. R. (2005) Chem. Rev. 105, 543-558
49. Yaggi, N. F., and Douglas, K. T. (1977) J. Am. Chem. Soc. 99, 4844-4845
50. Douglas, K. T., Yaggi, N. F., and Mervis, C. M. (1981) J. Chem. Soc., Perkin Trans. 2, 171-174
51. Douglas, K. T. (1986) Acc. Chem. Res. 19, 186-192
52. Baldwin, J. E. (1976) J. Chem. Soc. Chem. Commun. 734-736