Product-regulation mechanisms for fatty acid biosynthesis catalyzed by Mycobacterium smegmatis FAS I

ChemBioChem

Volumn 8, Issue 15, 2007, Pages 1775-1780

  Papaioannou, Nikolaos ^a   Cheon, Hwan Sung ^a   Lian, Yiqian ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

Aggregation; Biosynthesis; Fatty acid polysaccharide complexation; Fatty acids; Organic synthesis

Indexed keywords

FATTY ACID; MATRIX METALLOPROTEINASE;

ARTICLE; BINDING AFFINITY; BIOSYNTHESIS; CATALYSIS; FLUORESCENCE; MASS SPECTROMETRY; MYCOBACTERIUM SMEGMATIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL;

BINDING SITES; CATALYSIS; FATTY ACID SYNTHETASE COMPLEX; FATTY ACIDS; MODELS, CHEMICAL; MYCOBACTERIUM SMEGMATIS; POLYSACCHARIDES, BACTERIAL;

MYCOBACTERIUM SMEGMATIS;

EID: 35348978364     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200700380     Document Type: Article

References (35)

1. World Health Organization (WHO), tuberculosis fact sheet No. 104; http://www.who.int/mediacentre/factsheets/fs104/en/index.html, revised March 2007.
2. World Health Organization (WHO), leprosy fact sheet No. 101; http:// www.who.int/mediacentre/factsheets/fs101/en/, revised October 2005.
3. Buruli Ulcer: Mycobacterium Ulcerans Infection (Eds.: K. Asiedu, R. Scherpbier, M. Ravinglione), World Health Organization, Geneva, 2000.
4. The Biology of the Mycobacteria, Vols. 1 & 2 (Eds.: C. Ratledge, J. Stanford), Academic Press, New York, 1982.
5. P. E. Kolattukudy, N. D. Fernandes, A. K. Azad, A. M. Fitzmaurice, T. D. Sirakova, Mol. Microbiol. 1997, 24, 263-270.
6. S. Khasnobis, V. E. Escuyer, D. Chatterjee, Expert Opin. Ther. Targets 2002, 6, 21-40.
7. P. J. Brennan, H. Nikaido, Annu. Rev. Biochem. 1995, 64, 29-63.
8. B. J. Rawlings, Nat. Prod. Rep. 1998, 15, 275-308.
9. S. Smith, A. Witkowski, A. K. Joshi, Prog. Lipid Res. 2003, 42, 289-317.
10. K. Bloch in Advances in Enzymology and Related Areas of Molecular Biology, Vol. 45 (Ed.: A. Meister), Wiley, New York, 1977, pp. 1-85.
11. O. Zimhony, C. Vilcheze, W. R. Jacobs, Jr., J. Bacteriol. 2004, 186, 4051-4055.
12. D. N. Brindley, S. Matsumura, K. Bloch, Nature 1969, 224, 666-669.
13. M. Ilton, A. W. Jevans, E. D. McCarthy, D. Vance, H. B. White III, K. Bloch, Proc. Natl. Acad. Sci. USA 1971, 68, 87-91.
14. G. R. Gray, C. E. Ballou, J. Biol. Chem. 1971, 246, 6835-6842.
15. S. K. Maitra, C. E. Ballou, J. Biol. Chem. 1977, 252, 2459-2469.
16. G. Tuffal, R. Albigot, M. Riviere, G. Puzo, Glycobiology 1998, 8, 675-684.
17. M. C. Hsu, J. Lee, Y. Kishi, J. Org. Chem. 2007, 72, 1931-1940.
18. M. Meppen, Y. Wang, H.-S. Cheon, Y. Kishi, J. Org. Chem. 2007, 72, 1941-1950.
19. a)H.-S. Cheon, Y. Lian, Y. Kishi, Org. Lett. 2007, 9, 3323-3326;
20. b) H.-S. Cheon, Y. Lian, Y. Kishi, Org. Lett. 2007, 9, 3327-3329.
21. Y. Machida, K. Bloch, Proc. Natl. Acad. Sci. USA 1973, 70, 1146-1148.
22. J. E. Maggio, Proc. Natl. Acad. Sci. USA 1980, 77, 2582-2586.
23. T. Kiho, C. E. Ballou, Biochemistry 1988, 27, 5824-5828.
24. Y. Wang, J. Ma, H.-S. Cheon, Y. Kishi, Angew. Chem. 2007, 119, 1355-1358;
25. Angew. Chem. Int. Ed. 2007, 46, 1333-1336.
26. H.-S. Cheon, Y. Wang, J. Ma, Y. Kishi, ChemBioChem 2007, 8, 353-359.
27. W. I. Wood, D. O. Peterson, K. Bloch, J. Biol. Chem. 1978, 253, 2650-2656.
28. P. K. Flick, K. Bloch, J. Biol. Chem. 1974, 249, 1031-1036.
29. D. O. Peterson, K. Bloch, J. Biol. Chem. 1977, 252, 5735-5739.
30. S. J. Wakil, Biochemistry 1989, 28, 4523-4530.
31. It is generally accepted that animal FAS I releases its product as free fatty acids by the pathway catalyzed by a thioesterase (TE), whereas yeast and mycobacteria FAS I release palmityl-CoA by the pathway catalyzed by malonyl/palmitoyl transacylase (MPT). Interestingly, however, both TE and MPT are known to contain the same peptide sequence of "-Gly-X-Ser-Y-Gly-" in the active site of their domains. For details, see refs. [9] and [28], and: a) E. Schweizer, J. Hofmann, Microbiol. Mol. Biol. Rev. 2004, 68, 501-517;
32. b) C.-Y. Yang, W.-Y. Huang, S. Chirala, S. J. Wakil, Biochemistry 1988, 27, 7773-7777;
33. c) N. D. Fernandes, P. E. Kolattukudy, Gene 1996, 170, 95-99;
34. d) H.-P. Stuible, C. Wagner, I. Andreou, G. Huter, J. Haselmann, E. Schweizer, J. Bacteriol. 1996, 178, 4787-4793.
35. S. Kikuchi, D. L. Rainwater, P. E. Kolattukudy, Arch. Biochem. Biophys. 1992, 295, 318-326.