Origin of the β-lactam carbons in clavulanic acid from an unusual thiamine pyrophosphate-mediated reaction [3]

Journal of the American Chemical Society

Volumn 121, Issue 39, 1999, Pages 9223-9224

  Khaleeli, Nusrat ^a   Li, Rongfeng ^a   Townsend, Craig A ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM; CARBON; CLAVULANIC ACID; COCARBOXYLASE;

BIOSYNTHESIS; CONTROLLED STUDY; ENZYME BINDING; ENZYME MECHANISM; ENZYME METABOLISM; ENZYME PURIFICATION; ISOMERISM; LETTER; NONHUMAN; STEREOCHEMISTRY;

EID: 0032877650     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9923134     Document Type: Letter

References (20)

1. Bush, K.; Jacoby, G. A.; Medeiros, A. A. Antimicrob. Agents Chemother. 1995, 39, 1211-1233.
2. Page, M. I.; Laws, A. P. J. Chem. Soc., Chem. Commun. 1998, 1609-1617.
3. Townsend, C. A.; Ho, M.-F. J. Am. Chem. Soc. 1985, 107, 1065-1066.
4. Valentine, B. P.; Bailey, C. R.; Doherty, A.; Morris, J.; Elson, S. W.; Baggaley, K. H.; Nicholson, N. H. J. Chem. Soc., Chem. Commun. 1993, 1210-1211.
5. Elson, S. W.; Oliver, R. S. J. Antibiot. 1978, 31, 586-592.
6. Townsend, C. A.; Ho, M.-F. J. Am. Chem. Soc. 1985, 107, 1066-1068.
7. Pitlik, J.; Townsend, C. A. J. Chem. Soc., Chem. Commun. 1997, 225-226.
8. Elson, S. W.; Baggaley, K. H.; Davison, M.; Fulston, M.; Nicholson, N. H.; Risbridger, G. D.; Tyler, J. W. J. Chem. Soc., Chem. Commun. 1993, 1212-1214.
9. Stirling, I.; Elson, S. W. J. Antibiot. 1979, 32, 1125-1129.
10. Thirkettle, J. E.; Baldwin, J. E.; Edwards, J.; Griffin, J. P.; Schofield, C. J. J. Chem. Soc., Chem. Commun. 1997, 1025-1026.
11. Townsend, C. A.; Mao, S.-S. J. Chem. Soc., Chem. Commun. 1987, 86-89.
12. Lloyd, M. D.; Merritt, K. D.; Lee, V.; Sewell, T.; Wha-Son, B.; Baldwin, J. E.; Schofield, C. J.; Elson, S. W.; Baggaley, K. H.; Nicholson N. H. Tetrahedron 1999, 55, 10201-10220.
13. Mcllwaine, D. B.; Townsend, C. A. J. Chem. Soc., Chem. Commun. 1993, 1346-1347.
14. Basak, A.; Salowe, S. P.; Townsend, C. A. J. Am. Chem. Soc. 1990, 112, 1654-1656.
15. Bachmann, B. O.; Li, R.; Townsend, C. A. Proc. Natl. Acad. Sci., U.S.A. 1998, 95, 9082-9086.
16. McNaughton, H. J.; Thirkettle, J. E.; Zhang, Z.; Schofield, C. J.; Jensen, S. E.; Barton, B.; Greaves, P. J. Chem. Soc., Chem. Commun. 1998, 2325-2326.
17. Busby R. W.; Chang, M. D.-T.; Busby, R. C.; Wimp, J.; Townsend, C. A. J. Biol. Chem. 1995, 270, 4262-4269.
18. 2, 2 mM EDTA, 1 mM DTT, and 0.5 mM TPP.
19. Blacklow, S. C.; Raines, R. T.; Lim, W. A.; Zamore, P. D.; Knowles, J. R. Biochemistry 1988, 27, 1158-1167.
20. Racker, E. Methods Enzymol. 1957, 3, 293-296.