Plant-like biosynthetic pathways in bacteria: From benzoic acid to chalcone

Journal of Natural Products

Volumn 65, Issue 12, 2002, Pages 1956-1962

  Moore, Bradley S ^a,b   Hertweck, Christian ^b,c   Hopke, Jörn N ^a,b,d   Izumikawa, Miho ^a   Kalaitzis, John A ^a   Nilsen, George ^a   O'Hare, Thomas ^a,e   Piel, Jörn ^b,f   Shipley, Paul R ^a,g   Xiang, Longkuan ^a   Austin, Michael B ^h   Noel, Joseph P ^h  

^a UNIVERSITY OF ARIZONA   (United States)

^b UNIVERSITY OF WASHINGTON   (United States)

^c SALK INSTITUTE FOR BIOLOGICAL STUDIES   (United States)

^d HANS KNÖLL INSTITUTE   (Germany)

^e Massachussetts U   (United States)

^f OREGON HEALTH AND SCIENCE UNIVERSITY   (United States)

^g MAX PLANCK INSTITUTE FOR CHEMICAL ECOLOGY   (Germany)

^h OKANAGAN UNIVERSITY COLLEGE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

1,3,6,8 TETRAHYDROXYNAPHTHALENE SYNTHASE; ANTIBIOTIC AGENT; BACTERIAL PROTEIN; BENZOIC ACID; BENZOIC ACID DERIVATIVE; BENZOYL COENZYME A; CHALCONE; CHALCONE SYNTHASE; CINNAMIC ACID; ENTEROCIN; PHENYLALANINE; PHENYLALANINE AMMONIA LYASE; POLYKETIDE SYNTHASE; UNCLASSIFIED DRUG; VEGETABLE PROTEIN;

BACTERIUM; BIOINFORMATICS; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME STRUCTURE; GENE INACTIVATION; GENE SEQUENCE; MOLECULAR CLONING; MOLECULAR MODEL; NONHUMAN; PLANT; REVIEW; STREPTOMYCES; STREPTOMYCES COELICOLOR;

ACYL COENZYME A; ACYLTRANSFERASES; BENZOIC ACID; BRIDGED COMPOUNDS; CATALYSIS; CHALCONE; FLAVONOIDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MULTIENZYME COMPLEXES; PHENYLALANINE AMMONIA-LYASE; PHENYLPROPIONATES; PLANTS; PROTEIN CONFORMATION; STREPTOMYCES;

BACTERIA (MICROORGANISMS); STREPTOMYCES; STREPTOMYCES COELICOLOR; STREPTOMYCES MARITIMUS; UNCULTURED ACTINOMYCETE;

EID: 12244303620     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np020230m     Document Type: Review

References (42)

1. Based on an ASP Matt Suffness Award lecture at the 42nd Annual Meeting of the American Society of Pharmacognosy, Oaxaca, Mexico on July 18, 2001.
2. Langer, B.; Röther, D.; Rötey, J. Biochemistry 1997, 36, 10867-10871.
3. Ferrer, J.-L.; Jez, J. M.; Bowman, M. E.; Dixon, R. A.; Noel, J. P. Nature Struct. Biol. 1999, 6, 775-784.
4. Piel, J.; Hoang, K.; Moore, B. S. J. Am. Chem. Soc. 2000, 122, 5415-5416.
5. Piel, J.; Hertweck, C.; Shipley, P. R.; Hunt, D. M.; Newman, M. S.; Moore, B. S. Chem. Biol. 2000, 7, 943-955.
6. Hertweck, C.; Moore, B. S. Tetrahedron 2000, 56, 9115-9120.
7. Hertweck, C.; Jarvis, A. P.; Xiang, L.; Moore, B. S.; Oldham, N. J. ChemBioChem 2001, 2, 784-786.
8. Moore, B. S.; Hopke, J. N. ChemBioChem 2001, 2, 35-38.
9. Funa, N.; Ohnishi, Y.; Fujii, I.; Shibuya, M.; Ebizuka, Y.; Horinouchi, S. Nature 1999, 400, 897-899.
10. Funa, N.; Ohnishi, Y.; Ebizuka, Y.; Horinouchi, S. J. Biol. Chem. 2002, 277, 4628-4635.
11. Pfeifer, V.; Nicholson, G. J.; Ries, J.; Recktenwald, J.; Schefer, A. B.; Shawky, R. M.; Schroder, J.; Wohlleben, W.; Pelzer, S. J. Biol. Chem. 2001, 276, 38370-38377.
12. Li, T.-L.; Choroba, O. W.; Hong, H.; Williams, D. H.; Spencer, J. B. Chem. Commun. 2001, 2156-2157.
13. Chen, H. W.; Tseng, C. C.; Hubbard, B. K.; Walsh, C. T. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 14901-14906.
14. Pathirana, C.; Jensen, P. R.; Fenical, W. Tetrahedron Lett. 1992, 33, 7663-7666.
15. Sitachitta, N.; Gadepalli, M.; Davidson, B. S. Tetrahedron 1996, 52, 8073-8080.
16. Seto, H.; Sato, T.; Urano, S.; Uzawa, J.; Yonehara, H. Tetrahedron Lett. 1976, 4367-4370.
17. Shen, Y.; Yoon, P.; Yu, T.-W.; Floss, H. G.; Hopwood, D. A.; Moore, B. S. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 3622-3627.
18. Hopwood, D. A. Chem. Rev. 1997, 97, 2465-2497.
19. Rawlings, B. J. Nat. Prod. Rep. 1999, 16, 425-484.
20. Moore, B. S.; Hertweck, C. Nat. Prod. Rep. 2002, 19, 70-99.
21. Wilkinson, C. J.; Frost, E. J.; Staunton, J.; Leadlay, P. F. Chem. Biol. 2001, 8, 1197-1208.
22. Ribnicky, D. M.; Shulaev, V.; Rasidn, I. Plant Physiol. 1998, 118, 565-572.
23. Jarvis, A. P.; Schaaf, O.; Oldham, N. J. Planta 2000, 212, 119.
24. Schneider, S.; Mohamed, M. E.; Fuchs, G. Arch. Microbiol. 1997, 168, 310-320.
25. Bjorklund, J. A.; Leete, E. Phytochemistry 1992, 31, 3883-3887.
26. He, X.-Y.; Yang, S.-Y. Biochemistry 1997, 36, 11044-11049.
27. Xiang, L.; Moore, B. S. J. Biol. Chem. 2002, 277, 32505-32509.
28. Xiang, L.; Moore, B. S. J. Bacteriol., accepted for publication.
29. Schwede, T. F.; Rétey, J.; Schulz, G. E. Biochemistry 1988, 27, 5355-5361.
30. Xiang, L.; Kalaitzis, J. A.; Nilsen, G.; Chen, L.; Moore, B. S. Org. Lett. 2002, 4, 957-960.
31. Schröder, J. In Comprehensive Natural Products Chemistry; Sankawa, U., Ed.; Elsevier: Amsterdam, 1999; Vol. 1, pp 749-771.
32. Jez, J. M.; Bowman, M. E.; Noel, J. P. Biochemistry 2001, 40, 14829-14838.
33. Jez, J. M.; Austin, M. B.; Ferrer, J. L.; Bowman, M. E.; Schröder, J.; Noel, J. P. Chem. Biol. 2000, 7, 919-930.
34. Lukacin, R.; Schreiner, S.; Matern, U. FEBS Lett. 2001, 508, 413-417.
35. Bangera, M. G.; Thomashow, L. S. J. Bacteriol. 1999, 181, 3155-3163.
36. Mavrodi, O. V.; Gardener, B. B. M.; Mavrodi, D. V.; Bonsall, R. F.; Weller, D. M.; Thomashow, L. S. Phytopathology 2001, 91, 35-43.
37. Bentley, S. D.; Chater, K. F.; Cerdeño-Tárraga, A.-M.; Challis, G. L.; Thomson, N. R.; James, K. D.; Harris, D. E.; Quail, M. A.; Kieser, H.; Harper, D.; Bateman, A.; Brown, S.; Chandra, G.; Chen, C. W.; Collins, M.; Cronin, A.; Fraser, A.; Goble, A.; Hidalgo, J.; Hornsby, T.; Howarth, S.; Huang, C.-H.; Kieser, T.; Larke, L.; Murphy, L.; Oliver, K.; O'Niel, S.; Rabbinowitsch, E.; Rajandream, M.-A.; Rutherford, K.; Rutter, S.; Seeger, K.; Saunders: D.; Sharp, S.; Squares, R.; Squares, S.; Taylor, K.; Warren, T.; Wietzorrek, A.; Woodward, J.; Barrell, B. G.; Parkhill, J.; Hopwood, D. A. Nature 2002, 417, 141-147.
38. Shin-ya, K.; Furihata, K.; Hayakawa, Y.; Seto, H. Tetrahedron Lett. 1990, 31, 6025-6026.
39. Funayama, S.; Ishibashi, M.; Komiyama, K.; Ōmura, S. J. Org. Chem. 1990, 55, 1132-1133.
40. Rohmer, M. Nat. Prod. Rep. 1999, 16, 565-574.
41. Rohdich, F.; Kis, K.; Bacher, A.; Eisenreich, W. Curr. Opin. Chem. Biol. 2001, 5, 535-540.
42. Seto, H.; Watanabe, H.; Furihata, K. Tetrahedron Lett. 1996, 37, 7979-7982.