Biosynthesis of carbapenem antibiotics: New carbapenam substrates for carbapenem synthase (carC)

ChemBioChem

Volumn 5, Issue 6, 2004, Pages 879-882

  Sleeman, Mark C ^b   Smith, Paul ^a   Kellam, Barrie ^a   Chhabra, Siri Ram ^a   Bycroft, Barrie W ^a   Schofield, Christopher J ^b  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Antibiotics; Biosynthesis; Carbapenem; Oxoglutarate; Oxygenase

Indexed keywords

ANTIBIOTIC AGENT; ASCORBIC ACID; CARBAPENEM DERIVATIVE; CARBAPENEM SYNTHASE; SYNTHETASE; UNCLASSIFIED DRUG;

ANTIBIOTIC BIOSYNTHESIS; ANTIBIOTIC RESISTANCE; ARTICLE; CATALYSIS; CATALYST; CIS TRANS ISOMERISM; CORRELATION ANALYSIS; DRUG ACTIVITY; DRUG FORMULARY; DRUG SCREENING; ENZYME SUBSTRATE; EPIMERIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MOLECULAR INTERACTION; OXIDATION KINETICS; PRIORITY JOURNAL; REACTION ANALYSIS; SPECTRAL SENSITIVITY; STATISTICAL SIGNIFICANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TECHNIQUE;

ANTI-BACTERIAL AGENTS; CARBAPENEMS; CATALYSIS; KETOGLUTARIC ACIDS; MODELS, CHEMICAL; OXYGENASES; STEREOISOMERISM;

EID: 4043086511     PISSN: 14394227     EISSN: None     Source Type: Journal    
DOI: 10.1002/cbic.200300908     Document Type: Article

References (22)

1. D. M. Livermore, N. Woodford, Curr. Opin. Microbiol. 2000, 3, 489.
2. S. J. McGowan, M. Sebaihia, S. O'Leary, K. R. Hardie, P. Williams, G. S. A. B. Stewart, B. W. Bycroft, G. P. C. Salmond, Mol. Microbiol. 1997, 26, 545.
3. L. E. Nunez, C. Mendez, A. F. Brana, G. Blanco, J. A. Salas, Chem. Biol. 2003, 10, 301.
4. S. Derzelle, E. Duchaud, F. Kunst, A. Danchin, P. Bertin, Appl. Environ. Microbiol. 2002, 68, 3780.
5. R. Li, A. Stapon, J. T. Blanchfield, C. A. Townsend, J. Am. Chem. Soc. 2000, 122, 9296.
6. Analysis of a mutant strain of Pectobacterium carotovora defective in CarC results in the accumulation in the culture medium of only the (3S,5S)-carbapenam 2 (Bycroft et al., unpublished results).
7. J. Zhou, W. L. Kelly, B. O. Bachmann, M. Gunsior, C. A. Townsend, E. I. Solomon, J. Am. Chem. Soc. 2001, 123, 7388.
8. M. D. Lloyd, K. D. Merritt, V. Lee, T. J. Sewell, B. Wha-Son, J. E. Baldwin, C. J. Schofield, S. W. Elson, K. H. Baggaley, N. H. Nicholson, Tetrahedron 1999, 55, 10 201.
9. I. J. Clifton, L. X. Doan, M. C. Sleeman, M. Topf, H. Suzuki, R. C. Wilmouth, C. J. Schofield, J. Biol. Chem. 2003, 278, 20843.
10. A. Stapon, R. Li, C. A. Townsend, J. Am. Chem. Soc. 2003, 125, 8486.
11. B. W. Bycroft, C. Maslen, S. J. Box, A. G. Brown, J. W. Tyler, J. Chem. Soc. Chem. Commun. 1987, 1623.
12. B. W. Bycroft, S. R. Chhabra, B. Kellam, P. Smith, Tetrahedron Lett. 2003, 44, 973.
13. H. Tanaka, H. Sakagami, K. Ogasawara, Tetrahedron Lett. 2002, 43, 93.
14. B. Gerratana, A. Stapon, C. A. Townsend, Biochemistry 2003, 42, 7836.
15. B. Kellam, Ph. D. thesis, University of Nottingham (UK), 1996.
16. A. Avenoza, J. I. Barriobero, J. H. Busto, J. M. Peregrina, J. Org. Chem. 2003, 68, 2889.
17. S. M. Schmitt, D. B. R. Johnston, B. G. Christensen, J. Org. Chem. 1980, 45, 1142.
18. R. Myllyla, K. Majamaa, V. Gunzler, H. M. Hanauske-Abel, K. I. Kivirikko, J. Biol. Chem. 1984, 259, 5403.
19. M. W. Vetting, S. L. Roderick, M. Yu, J. S. Blanchard, Protein Sci. 2003, 12, 1954.
20. K. Laumen, E. H. Reimerdes, M. Schneider, H. Gorisch, Tetrahedron Lett. 1985, 26, 407.
21. A. Stapon, R. Li, C. A. Townsend, J. Am. Chem. Soc. 2003, 125, 15 746.
22. M. C. Sleeman, C. J. Schofield, J. Biol. Chem. 2004, 279, 6730.