Structure of a hydroxymycolic acid potentially involved in the synthesis of oxygenated mycolic acids of the Mycobacterium tuberculosis complex

European Journal of Biochemistry

Volumn 250, Issue 3, 1997, Pages 758-763

  Quémard, Annaïk ^a   Lanéelle, Marie Antoinette ^a   Marrakchi, Hédia ^a   Promé, Danielle ^a   Dubnau, Eugenie ^b   Daffé, Mamadou ^a  

^a INSTITUT DE PHARMACOLOGIE ET DE BIOLOGIE STRUCTURALE   (France)

^b PUBLIC HEALTH RESEARCH INSTITUTE   (United States)

Author keywords

Biosynthesis; Hydroxymycolic acid; Ketomycolic acid; Mycobacterium tuberculosis complex; Structure

Indexed keywords

HYDROXYMYCOLIC ACID; MYCOLIC ACID; OXOMYCOLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL MEMBRANE; CHEMICAL STRUCTURE; MASS SPECTROMETRY; MYCOBACTERIUM BOVIS; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

BACTERIA (MICROORGANISMS); MYCOBACTERIUM; MYCOBACTERIUM BOVIS BCG; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS;

EID: 0031574208     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1432-1033.1997.00758.x     Document Type: Article

References (34)

1. Asselineau, J. & Lederer, E. (1950) Structure of the mycolic acids of Mycobacteria, Nature 166, 782-783.
2. Daffé, M. & Draper, P. (1998) The envelope layers of mycobacteria with reference to their pathogenicity, Adv. Microbial Physiol. 39, 131-203.
3. Lacave, C., Lanéelle, M. A. & Lanéelle, G. (1990) Mycolic acid synthesis by Mycobacterium aurum cell-free extracts, Biochim. Biophys. Acta 1042, 315-323.
4. Shimakata, T., Iwaki, M. & Kusaka, T. (1984) In vitro synthesis of mycolic acids by the fluffy layer fraction of Bacterionema matruchotii, Arch. Biochem. Biophys. 229, 329-339.
5. 32-β-ketoester from palmitic acid in a cell-free system of Corynebacterium diphtheriae, Biochim. Biophys, Acta 326, 52-62.
6. Gastambide-Odier, M. & Lederer, E. (1960) Biosynthèse de l'acide corynomycolique à partir de deux molécules d'acide palmitique, Biochem. Z. 333, 285-295.
7. Etemadi, A. H. & Lederer, E. (1965) Biosynthèse de l'acide α-smegma-mycolique, Biochim. Biophys. Acta 98, 160-167.
8. Lanéelle, G. (1989) Mycolic acid metabolism, Biosynthesis of complex lipids, Acta Leprol. 7 (Suppl. 1), 65-73.
9. Lopez-Marin, L. M., Quémard, A., Lanéelle, G. & Lacave, C. (1991) Ethylenic mycolic acid biosynthesis: extension of the biosynthetic model using cell-free extract of Mycobacterium aurum and Mycobacterium smegmatis, Biochim. Biophys. Acta 1086, 22-28.
10. Takayama, K. & Davidson, L. A. (1979) Isonicotinic acid hydrazide, in Mechanism of action of antimicrobial agents. Antibiotics (Hahn, F. E., ed.) vol. 5, part 1, pp. 98-119, Springer-Verlag, Berlin.
11. Jaureguiberry, G., Lenfant, M., Das, B. C. & Lederer, E. (1966) Sur le mécanisme des C-méthylations biologiques par la méthionine, Tetrahedron Suppl. 8 part 1, 27-32.
12. Etemadi, A. H. & Gasche, J. (1965) Sur l'origine biogénétique du 2-eicosanol et du 2-octadecanol de Mycobacterium avium, Bull. Soc. Chim. Biol. 47, 2095-2104.
13. Lacave, C., Lanéelle, M. A., Daffé, M., Montrozier, H., Rols, M. P. & Asselineau, C. (1987) Etude structurale et métabolique des acides mycoliques de Mycobacterium fortuitum, Eur. J. Biochem. 163, 369-378.
14. Gastambide-Odier, M., Delaumeny, J. M. & Lederer, E. (1964) Mise en évidence de cycles propaniques dans divers acides mycoliques de souches humaines et bovines de Mycobacterium tuberculosis, C. R. Acad. Sci. Paris 259, 3404-3407.
15. Quémard, A., Sacchettini, J. C., Dessen, A., Vilchèze, C., Bittman, R., Jacobs, W. R. Jr & Blanchard, J. S. (1995) Enzymatic characterization of the target for isoniazid in Mycobacterium tuberculosis, Biochemistry 34, 8235-8241.
16. Dessen, A., Quémard, A., Blanchard, J. S., Jacobs, W. R. Jr & Sacchettini, J. C. (1995) Crystal structure and function of the isoniazid target of Mycobacterium tuberculosis, Science 267, 1638-1641.
17. Banerjee, A., Dubnau, E., Quémard, A., Balasubramanian, V., Um, K. S., Wilson, T., Collins, D., de Lisle, G. & Jacobs, W. R. Jr (1994) InhA, a gene encoding a target for isoniazid and ethionamide in Mycobacterium tuberculosis, Science 263, 227-230.
18. Yuan, Y., Lee, R. E., Besra, G. S., Belisle, J. T. & Barry, C. E. (1995) Identification of a gene involved in the biosynthesis of cyclopropanated mycolic acids in Mycobacterium tuberculosis, Proc. Natl Acad. Sci. USA 92, 6630-6634.
19. George, K. M., Yuan, Y. Sherman, D. R. & Barry, C. E. (1995) The biosynthesis of cyclopropanated mycolic acids in Mycobacterium tuberculosis, J. Biol. Chem. 270, 27292-27298.
20. Dubnau, E., Lanéelle, M. A., Soares, S., Bénichou, A., Vaz, T., Promé, D., Promé, J. C., Daffé, M. & Quémard, A. (1997) Mycobacterium bovis BCG genes involved in the biosynthesis of cyclopropyl keto- and hydroxy- mycolic acids, Mol. Microbiol. 23, 313-322.
21. Yuan, Y. & Barry, C. E. (1996) A common mechanism for the biosynthesis of methoxy and cyclopropyl mycolic acids in Mycobacterium tuberculosis, Proc. Natl Acad. Sci. USA 93, 12828-12833.
22. Asselineau, C., Clavel, S., Clément, F., Duffé, M., David, H., Lanéelle, M. A. & Promé, J. C. (1981) Constituants lipidiques de Mycobacterium leprae isolé de tatou infecté expérimentalement, Ann. Microbiol. (Inst. Pasteur) 132A, 19-30.
23. Daffé, M., Lanéelle, M. A., Asselineau, C., Lévy-Frébault, V. & David, H. (1983) Intérêt taxonomique des acides gras des mycobactéries: proposition d'une méthode d'analyse, Ann. Microbiol. (Inst. Pasteur) 134B, 241-256.
24. Daffé, M., Lanéelle, M. A. & Valero Guillen, P. L. (1988) Tetraenoic and pentaenoic mycolic acids from Mycobacterium thamnopheos. Structure, taxonomic and biosynthetic implications, Eur. J. Biochem. 177, 339-344.
25. Sweeley, C. C. Bentley, R., Makita, M. & Wells, W. W. (1963) Gasliquid chromatography of trimethylsilyl derivatives of sugars and related substances, J. Am. Chem. Soc. 85, 2497-2507.
26. Minnikin, D. E. (1982) Lipids: complex lipids, their chemistry, biosynthesis and roles, in The biology of the Mycobacteria (Ratledge, C. & Stanford, J., eds) vol. 1, pp. 95-184, Academic Press, San Diego CA.
27. Asselineau, C., Tocanne, G. & Tocanne, J. F. (1970) Stéréochimie des acides mycoliques, Bull. Soc. Chim. France 4, 1455-1459.
28. Daffé, M., Lanéelle, M. A. & Lacave, C. (1991) Structure and stereochemistry of mycolic acids of Mycobacterium marinum and Mycobacterium ulcerans, Res. Microbiol. 142, 397-403.
29. Asselineau, J. & Asselineau, C. (1966) Stéréochimie de l'acide corynomycolique, Bull. Soc. Chim. France 6, 1992-1999.
30. Daffé, M. Lanéelle, M. A., Puzo, G. & Asselineau, C. (1981) Acide mycolique epoxydique: un nouveau type d'acide mycolique, Tetrahedr. Lett. 22, 4515-4516.
31. Luquin, M., Roussel, J., Lopez-Calahorra, F., Lanéelle, G., Ausina, V. & Lanéelle, M. A. (1990) A novel mycolic acid in a Mycobacterium sp. from the environment, Eur. J. Biochem. 192, 753-759.
32. 1 de Mycobacterium tuberculosis, Bull. Soc. Chim. France, 427-431.
33. Asselineau, J. & Gendre, T. (1954) Sur les acides mycoliques de trois souches humaines de Mycobacterium tuberculosis: H37Ra, H37Rv et un mutant H37Rv streptomycino-résistant, Bull. Soc. Chim. France, 1226-1233.
34. Davidson, L. A., Draper, P. & Minnikin, D. E. (1982) Studies on the mycolic acids from the walls of Mycobacterium microti, J. Gen. Microbiol. 128, 823-828.