Probable role of clavaminic acid as the terminal intermediate in the common pathway to clavulanic acid and the antipodal clavam metabolites

Journal of the American Chemical Society

Volumn 119, Issue 10, 1997, Pages 2348-2355

  Egan, Laura A ^a   Busby, Robert W ^a   Iwata Reuyl, Dirk ^a,b   Townsend, Craig A ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b PORTLAND STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAMASE INHIBITOR; CARBON 13; CLAVAM DERIVATIVE; CLAVAMINIC ACID; CLAVULANIC ACID; RECOMBINANT ENZYME; UNCLASSIFIED DRUG; VALCLAVAM;

ARTICLE; BIOSYNTHESIS; DRUG SYNTHESIS; ENZYME ACTIVITY; ISOTOPE LABELING; STREPTOMYCES;

EID: 0030991157     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963107o     Document Type: Article

References (47)

1. Townsend, C. A. Biochem. Soc. Trans. 1993, 21, 208-213.
2. Müller, J.-C.; Toome, V.; Pruess, D. L.; Blount, J. F.; Weigele, M. J. Antibiot. 1983, 36, 217-225.
3. Brown, D.; Evans, J. R.; Fletton, R. A. J. Chem. Soc., Chem. Commun. 1979, 282-283.
4. Röhl, F.; Rabenhorst, J.; Zähner, H. Arch. Microbiol. 1987, 147, 315-320.
5. Baldwin, J. E.; Claridge, T. D. W.; Goh, K.-C.; Keeping, J. W.; Schofield, C. J. Tetrahedron Lett. 1993, 34, 5645-5648.
6. Janc, J. W.; Egan, L. A.; Townsend, C. A. Bioorg. Med. Chem. Lett. 1993, 3, 2213-2216.
7. Postels, H.-T.; König, W. A. Tetrahedron Lett. 1994, 35, 4535-4538.
8. Wanning, M.; Zähner, H.; Krone, B.; Zeeck, A. Tetrahedron Lett. 1981, 22, 2539-2540.
9. Townsend, C. A.; Ho, M.-F. J. Am. Chem. Soc. 1985, 707, 1065-1066.
10. 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.
11. Elson, S. W.; Baggaley, K. H.; Davidson, M.; Fulston, M.; Nicholson, N. H.; Risbridger, G. D.; Tyler, J. W. J. Chem. Soc., Chem. Commun. 1993, 1212-1214.
12. Elson, S. W.; Baggaley, K. H.; Fulston, M.; Nicholson, N. H.; Tyler, J. W.; Edwards, J.; Holms, H.; Hamilton, L; Mousdale, D. M. J. Chem. Soc., Chem. Commun. 1993, 1211-1212,
13. Baldwin, J. E.; Merritt, K. D.; Schofield, C. J.; Elson, S. W.; Baggaley, K. H. J. Chem. Soc., Chem. Commun. 1993, 1301-1302.
14. Aidoo, K. A.; Wong, A.; Alexander, D. C.; Rittammer, R. A. R.; Jensen, S. E. Gene 1994, 147, 41-46.
15. Wu, T. K.; Busby, R. W.; Houston, T. A.; McIlwaine, D. B.; Egan, L. A.; Townsend, C. A. J. Bacterial. 1995, 177, 3714-3720.
16. Baldwin, J. E.; Adlington, R. M.; Bryans, J. S.; Bringhen, A. O.; Coates, J. B.; Crouch, N. P.; Lloyd, M. D.; Schofield, C. J.; Elson, S. W.; Baggaley, K. H.; Cassells, R.; Nicholson, N. J. Chem. Soc., Chem. Commun. 1990, 617-619.
17. Salowe, S. P.; Krol, W. J.; Iwata-Reuyl, D.; Townsend, C. A. Biochemistry 1991, 30, 2281-2292.
18. Elson, S. W.; Baggaley, K. H.; Gillett, J.; Holland, S.; Nicholson, N. H.; Sime, J. T.; Woroniecki, S. R. J. Chem. Soc., Chem. Commun. 1987, 1736-1738.
19. Townsend, C. A.; Krol, W. J. J. Chem. Soc., Chem. Commun. 1988, 1234-1236.
20. Nicholson, N H.; Baggaley, K. H.; Casscls, R.; Davison, M.; Elson, S. W.; Fulston, M.; Tyler, J. W.; Woroniecki, S. R. J. Chem. Soc., Chem. Commun. 1994, 1281-1282.
21. Iwata-Reuyl, D.; Townsend, C. A. J. Am. Chem. Soc. 1992, 114, 2762-2763.
22. Townsend, C. A.; Ho, M.-F. J. Am. Chem. Soc. 1985, 107, 1066-1068.
23. Salowe, S. P.; Marsh, E. N.; Townsend, C. A. Biochemistry 1990, 29, 6499-6508.
24. Janc, J. W.; Egan, L. A.; Townsend, C. A. J. Biol. Chem. 1995, 270, 5399-5404.
25. Baldwin, J. E.; Fujishima, Y.; Goh, K. C; Schofield, C. J. Tetrahedron Lett. 1994, 35, 2783-2786.
26. Lawlor, E. J.; Elson, S. W.; Holland, S.; Cassels, R.; Hodgson, J. E.; Lloyd, M. D.; Baldwin, J. E.; Schofield, C. J. Tetrahedron 1994, 50, 8737-8748.
27. Busby, R. W.; Chang, M. D.-T.; Busby, R. C.; Wimp, J.; Townsend, C. A. J. Biol. Chem. 1995, 270, 4262-4269.
28. Such an enzymatic conversion has been carried out previously, although no experimental details were reported: Elson, S. W.; Baggaley, K. H.; Gillett, J.; Holland, S.; Nicholson, N. H.; Sime, J. T.; Woroniecki, S. R. J. Chem. Soc., Chem. Commun. 1987, 1739-1740.
29. Townsend, C. A.; Basak, A. Tetrahedron 1991, 47, 2591-2602.
30. Ishizumi, K.; Koga, K.; Yamada, S.-I. Chem. Pharm. Bull. 1968, 16, 492-497.
31. Stelakatos, G. C.; Paganou, A.; Zervas, L. J. Chem. Soc. C 1966, 1191-1199.
32. Kobayashi, T.; Iwano, Y.; Hirai, K. Chem. Pharm. Bull. 1978, 26, 1761-1767.
33. Pansare, S. V.; Vederas, J. C. J. Org. Chem. 1987, 52, 4804-4810.
34. Baggaley, K. H.; Elson, S. W.; Nicholson, N. H.; Sime, J. T. J. Chem. Soc., Perkin Trans, 1 1990, 1513-1520.
35. Iwata-Reuyl, D.; Basak, A.; Silverman, L. S.; Engle, C. A.; Townsend, C. A. J. Nat. Prod. 1993, 56, 1373-1396.
36. Bird, A. E.; Bellis, J. M.; Gasson, B. C. Analyst 1982, 107, 1241-1245.
37. Naegeli, H. U.; Loosli, H.-R.; Nussbaumer, A. J. Antibiot. 1986, 39, 516-524.
38. Baldwin, J. E.; Goh, K.-C.; Schofield, C. J. Tetrahedron Lett. 1994, 35, 2779-2782.
39. Egan, L. A.; Townsend, C. A., Unpublished results.
40. Vederas, J. C. Nat. Prod. Rep. 1987, 4, 277-337.
41. Marsh, E. N.; Chang, M. D.-T.; Townsend, C. A. Biochemistry 1992, 31, 12648-12657.
42. Paradkar, A. S.; Jensen, S. E. J. Bacteriol. 1995, 177, 1307-1314.
43. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: New York, 1988.
44. Bradford, M. M. Anal. Biochem. 1976, 72, 248-254.
45. Laemmli, U. K. Nature (London) 1970, 227, 680-685.
46. Maniatis, T.; Fritsch, E. F.; Sambrook, J. Molecular Cloning. A Laboratory Manual; Cold Spring Harbor Laboratory: New York, 1982.
47. Wanning, M. Ph.D Thesis, University of Tübingen, Tübingen, Germany, 1980.