Configurational analysis of cyclopropyl fatty acids isolated from Escherichia coli

Organic Letters

Volumn 8, Issue 1, 2006, Pages 79-81

  Stuart, Laura J ^a   Buck, James P ^a   Tremblay, Amy E ^a   Buist, Peter H ^a  

^a CARLETON UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

FATTY ACID;

ARTICLE; CHEMISTRY; ESCHERICHIA COLI; STEREOISOMERISM;

ESCHERICHIA COLI; FATTY ACIDS; STEREOISOMERISM;

EID: 30944450243     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052550d     Document Type: Article

References (29)

1. Grogan, D. W.; Cronan, J. E., Jr. Microbiol. Mol. Biol. 1997, 61, 429.
2. Cronan, J. E., Jr. Curr. Opin. Microbiol. 2002, 5, 202.
3. Bao, X.; Katz, S.; Pollard, M.; Ohlrogge, J. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 7172.
4. Glickman, M. S.; Cox, J. S.; Jacobs, W. R. Mol. Cell. 2000, 5, 717.
5. Huang, C.; Smith, C. V.; Glickman, M. S.; Jacobs, W. R.; Sacchettini, J. C. J. Biol. Chem. 2002, 277, 11559.
6. Molitor, E. J.; Paschal, B. M.; Liu, H.-w. ChemBioChem 2003, 4, 1352.
7. Iwig, D. F.; Booker, S. J. Biochemistry 2004, 43, 13496.
8. Iwig, D. F.; Grippe, A. T.; McIntyre, T. A.; Booker, S. J. Biochemistry 2004, 43, 13510.
9. Courtois, F.; Guerard, C.; Thomas, X.; Ploux, O. Eur. J. Biochem. 2004, 271, 4769.
10. Iwig, D. F.; Uchida, A.; Stromberg, J. A.; Booker, S. J. J. Am. Chem. Soc. 2005, 127, 11612.
11. Courtois, F.; Ploux, O. Biochemistry 2005, 44, 13583.
12. Lederer, E. Q. Rev. Chem. Soc. 1969, 23, 453.
13. Buist, P. H.; Maclean, D. B. Can. J. Chem. 1982, 60, 371.
14. Arigoni, D. Chimia 1987, 41, 9.
15. Cohen, T.; Herman, G.; Chapman, T. M.; Kuhn, D. J. Am. Chem. Soc. 1974, 96, 5627.
16. Buist, P. H.; Behrouzian, B. J. Am. Chem. Soc. 1998, 120, 871.
17. Law, J. H.; Zalkin, H.; Kaneshiro, T. Biochim. Biophys. Acta 1963, 70, 143.
18. Imai, N.; Sakamoto, K.; Takahashi, H.; Kobayashi, S. Tetrahedron Lett. 1994, 35, 7045.
19. 21
20. Coxon, G. D.; Al-Dulayymi, J. R.; Baird, M. S.; Knobl, S.; Roberts, E.; Minnikin, D. E. Tetrahedron: Asymmetry 2003, 14, 1211.
21. Lou, L.; Horikawa, M.: Kloster, R. A.; Hawryluk, N. A.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 8916.
22. Tocanne, J. F. Tetrahedron 1972, 28, 363.
23. 2 It is considered less likely that 2 is a chain elongation product derived from 1 or that 1 is a β-oxidation product of 2.
24. Tocanne, J. F.; Bergmann, R. G. Tetrahedron 1972, 28, 373.
25. Rasonyi, S. Diss. ETH # 11318, 1995.
26. Stuart, L. J.; Buist, P. H. Tetrahedron: Asymmetry 2004, 15, 401.
27. Mori, K.; Tashiro, T.; Akasaki, K.; Ohrui, H.; Fattorusso, E. Tetrahedron Lett. 2002, 43, 3719.
28. Buist, P. H.; Pon, R. A. J. Org. Chem. 1990, 55, 6240.
29. Ohlrogge, J. B.; Gunstone, F. D.; Ismail, I. A.; Lands, W. E. M. Biochim. Biophys. Acta 1976, 431, 257.