Synthesis and stereochemistry-activity relationship of small bacteriocin, an autoinducer of the symbiotic nitrogen-fixing bacterium rhizobium Leguminosarum

Organic Letters

Volumn 10, Issue 10, 2008, Pages 2047-2050

  Yajima, Arata ^a   Van Brussel, Anton A N ^b   Schripsema, Jan ^c,d   Nukada, Tomoo ^a   Yabuta, Goro ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE   (Japan)

^b LEIDEN UNIVERSITY   (Netherlands)

^c DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

^d UNIVERSIDADE ESTADUAL DO NORTE FLUMINENSE DARCY RIBEIRO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIOCIN; DRUG DERIVATIVE; GAMMA BUTYROLACTONE; HOMOSERINE LACTONE; NITROGEN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; MICROBIOLOGICAL EXAMINATION; RHIZOBIUM LEGUMINOSARUM; STEREOISOMERISM; SYNTHESIS;

4-BUTYROLACTONE; BACTERIOCINS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; NITROGEN; RHIZOBIUM LEGUMINOSARUM; STEREOISOMERISM;

EID: 47049089168     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8005198     Document Type: Article

References (40)

1. Fuqua, W. C.; Winans, S. C.; Greenberg, E. P. J. Bacterial. 1994, 176, 269-275.
2. (a) Kijne, J. W. Biological Nitrogen Fixation; Stacey, G., Burris, R. H., Evans, H. J., Eds.; Chapman and Hall: London. UK. 1992; pp 349-398.
3. (b) van Rhijn, P.; Vanderleyden, J. Microbiol. Rev. 1995, 59, 124-142.
4. (c) Oke, V.; Long, S. R. Curr. Opin. Microbiol. 1999. 2. 1299.
5. (d) Perret. X.; Staechelin. C; Broughton. W. J. Microbiol. Mol. Biol. Rev. 2000, 64, 180-201.
6. (a) Rodelas, B.; Lithgow, J. K.; Wisniewski-Dyé, F.; Hardman, A.; Wilkinson, A.; Economou, A.; William, P.; Downie, J. A. J. Bacterial. 1999, 181, 3816-3823.
7. (b) Thome, S. H.; Williams, H. D. J. Bacteriol. 1999, 181, 981-990.
8. (c) Lithgow, J. K.; Willkinson, A.; Hardman, A.; Rodelas, B.; Wisniewski-Dyé, F.; Williams, P.; Downie, J. A. Mol. Microbiol. 2000, 37, 81-97.
9. (d) Blosser-Middleton, R. S.; Gray, K. M. J. Bacterial. 2001. 183, 6171-6117.
10. Gray, K. M.; Pearson, J. P.; Downie, J. A.; Boboye, B. E. A.; Greenberg, E. P. J. Bacterial. 1996, 178, 372-376.
11. Hirsch, P. R. J. Gen. Microbiol. 1979, 113, 219-228.
12. Schripsema, J.; de Rudder, K. E. E.; van Vliet, T. B.; Lankhorst, P. P.; de Vroom. E.; Kijne, J. W.; van Brussel, A. A. N. J. Bacterial. 1996, 178, 366-371.
13. Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem, 1977, 42, 384-387.
14. (a) Fuqua, C.; Winans, S. C.; Greenberg, E. P. Annu. Rev. Microbiol. 1996, 50, 727-751.
15. (b) Gray, K. M. Trends Microbiol. 1997, 5, 184-188.
16. (c) Parsek, M. R.; Greenberg. E. P. Proc. Nat. Acad. Set USA 2000. 97, 8789-8793.
17. (d) Whitehead, N. A.; Barnard. A. M. L.; Slater, H.; Simpson, N. J. L.; Salmond, G. P. C. FEMS Microbiol. Rev. 2001, 25, 365-104.
18. (a) Mori, K. In The Total Synthesis of Natural Product; ApSimon, J., Ed.; Wiley-Interscience: New York, 1992; Vol. 9.
19. (b) Mori, K. Bioorg. Med. Chem. 2007, 15, 7505-7523.
20. Synthesis of 3 -hydroxyacyl HSLs: (a) Cao. J.-G.; Meighen, E. A. J. Bacterial. 1993, 175, 3856-3862.
21. (b) Chhabra, S. R.; Stead. P.; Bainton, N. J.; Salmond, G. P. C.; Stewart, G. S. A. B.; Williams, P.; Bycroft, B. W. J. Antibiot. 1993, 46, 441-454.
22. (c) Chhabra, S. R.; Harty, C; Hooi, D. S. W.; Daykin, M.; Williams, P.; Telford. G.; Pritcchard, D. I.; Bycroft, B. W. J. Med. Chem. 2003, 46, 97-104.
23. (d) Janssens, J. C. A.; Metzger, K.; Daniels, R.; Ptacek, D.; Verhoeven, T.; Habel, L. W.; Vanderleyden, J.; De Vos, D. E.; De Keersmaecker, S. C. J. Appl. Environ. Microbiol. 2007, 73, 535-544.
24. Huang, G.; Hollingsworth, R. I. Tetrahedron: Asymmetrv 1998, 9, 4113-4115.
25. Tamada, S.; Mori. K.; Matsui, M. Agric. Biol. Chem. 1978, 42, 191-192.
26. Yoon, N. M.; Choi, J. Tetrahedron Lett. 1996, 37, 1057-1060.
27. Downing, S. V.; Aguilar, E.; Meyers, A. I. J. Org. Chem. 1999, 64, 826-831.
28. (a) Nicolaou, K. C.; Li, J.; Zenke, G. Helv. Chim. Acta 2000, 83, 1977-2006.
29. (b) Mori, K.; Tashiro, T.; Akasaka, K.; Ohrui, H.; Fattorusso, E. Tetrahedron Lett. 2002, 43, 3719-3722.
30. (c) Tashiro, T.; Akasaka, K.; Ohrui, H.; Fattorusso, E.; Mori, K. Eur. J. Org. Chem. 2002, 3659-3665.
31. Krapcho, A. P. Synthesis 1982, 805-822.
32. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639-666.
33. Keck. G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995. 117, 2363-2364.
34. (a) Nagao. Y.; Hagiwara, Y.; Kumagai, T.; Ochiai, M.; Inoue. T.; Hashimoto. K.; Fujita, E. J. Org. Chem. 1986, 51, 2391-2393.
35. (b) Nagao, Y.; Dai, W.-M.; Ochiai, M.; Shiro, M. J. Org. Chem. 1989, 54, 5211-5217.
36. Yuasa, H.; Satoda, S.; Aoyama, M. Jpn. Kokai Tokkyo Koho 2003206254, 2003.
37. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983. 48, 4155-4156.
38. Smith, T. H.; Djang, M.; Velander, A. J.; Downey, C. W.; Carroll, K. A.; van Alphen, S. Org. Lett. 2004, 6, 2317-2320.
39. Laus. M. C.; van Brussel. A. A. N.; Kijne, J. W. Mol. Plant-Microb. Interact. 2005, 18, 533-538.
40. Hooykaas, P. J. J.; Schnijdewindt, F. G. M.; Schilperoort, R. A. Plasmid 1982, 8, 73-82.