Observation of an acryloyl-thiamin diphosphate adduct in the first step of clavulanic acid biosynthesis

Journal of the American Chemical Society

Volumn 129, Issue 51, 2007, Pages 15750-15751

  Merski, Matthew ^a   Townsend, Craig A ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLAMIDE DERIVATIVE; ACRYLIC ACID; CLAVULANIC ACID; GLYCERALDEHYDE 3 PHOSPHATE DEHYDROGENASE; OCTOPINE; THIAMIN DIPHOSPHATE; THIAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHROMATOGRAPHY; CHROMATOPHORE; DRUG SYNTHESIS; ENANTIOMER; ION EXCHANGE; OBSERVATION; PARTICLE SIZE; PROTEIN AGGREGATION; SEPARATION TECHNIQUE; SPECTROSCOPY;

BETA-LACTAMASES; CATALYSIS; CIRCULAR DICHROISM; CLAVULANIC ACID; ENZYME INHIBITORS; MODELS, CHEMICAL; SPECTROPHOTOMETRY, ULTRAVIOLET; THIAMINE PYROPHOSPHATE;

EID: 37548999032     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja076704r     Document Type: Article

References (25)

1. Elander, R. P. Appl. Microbiol. Biotechnol. 2003, 61, 385-392.
2. Townsend, C. A. Curr. Opin. Chem. Biol. 2002, 6, 583-589.
3. Khaleeli, N.; Li, R. F.; Townsend, C. A. J. Am. Chem. Soc. 1999, 121, 9223-9224 and refs cited therein.
4. Evans, D. A.; Fandrick, K. R.; Song, H. J. J. Am. Chem. Soc. 2005, 127, 8942-8943.
5. Engel, S.; Barak, Z.; Chipman, D. M.; Merchuk, J. C. J. Chromatogr., B: Biomed. Sci. Appl. 2000, 743, 281-286.
6. Pederson, R. L.; Liu, K. K. C.; Rutan, J. F.; Chen, L.; Wong, C. H. J. Org. Chem. 1990, 55, 4897-4901.
7. Sigma-Aldrich, Technical Bulletin.
8. Tittmann, K.; Golbik, R.; Uhlemann, K.; Khailova, L.; Schneider, G.; Patel, M.; Jordan, F.; Chipman, D. M.; Duggleby, R. G.; Hubner, G. Biochemistry 2003, 42, 7885-7891.
9. Webb, M. R. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 4884-4887.
10. Li, R. F.; Stapon, A.; Blanchfield, J. T.; Townsend, C. A. J. Am. Chem. Soc. 2000, 122, 9296-9297.
11. Mawhinney, T. P.; Madson, M. A. J. Org. Chem. 1982, 47, 3336-3339.
12. Gruys, K. J.; Halkides, C. J.; Frey, P. A. Biochemistry 1987, 26, 7575-7585.
13. Daigo, K.; Reed, L. J. J. Am. Chem. Soc. 1962, 84, 659-662.
14. Oka, Y.; Kishimot, S.; Hirano, H. Chem. Pharm. Bull. 1970, 18, 527-533.
15. Lienhard, G. E. J. Am. Chem. Soc. 1966, 88, 5642-5649.
16. White, F. G.; Ingraham, L. L. J. Am. Chem. Soc. 1962, 84, 3109-3111.
17. Ireland, R. E.; Liu, L. B. J. Org. Chem. 1993, 58, 2899-2899.
18. Iversen, P. E. Acta Chem. Scand. 1968, 22, 694-695.
19. Vaughan, W. R.; Carlson, R. D. J. Am. Chem. Soc. 1961, 83, 769-774.
20. Kosugi, M.; Koshiba, M.; Atoh, A.; Sano, H.; Migita, T. Bull. Chem. Soc., Jpn. 1985, 59, 677-679.
21. Nemeria, N.; Baykal, A.; Joseph, E.; Zhang, S.; Yan, Y.; Furey, W.; Jordan, . Biochemistry 2004, 43, 6565-6575.
22. Mataga, N.; Kubota, T. Molecular Interactions and Electronic Spectra; Marcel Dekker Inc.: New York, 1970; pp 371-484.
23. Sorensen, T. S. J. Am. Chem. Soc. 1965, 87, 5075-5084.
24. Hamer, F. M. The Cyanine Dyes and Related Compounds. In The Chemistry of Heterocyclic Compounds; Weissberger, A., Ed.; John Wiley & Sons: New York, 1969.
25. Kochendoerfer, G. G.; Lin, S. W.; Sakmar, T. P.; Mathies, R. A. Trends Biochem. Sci. 1999, 24, 300-305.