1887

Abstract

Total mycolic acid methyl ester fractions were isolated from 24 representatives of , (including BCG), , and . The total mycolate functional group composition was estimated from H-NMR spectra. Mycolates were separated into α-mycolates, methoxymycolates and ketomycolates and each class was further separated by argentation chromatography into mycolates with no double bonds, with one double bond and with one double bond. Mass spectrometry revealed the mycolate chain lengths and H-NMR the and double bond and cyclopropane ring content. The same species had similar mycolate profiles; the major type of each class had or cyclopropane rings and lacked double bonds. Minor proportions of possible unsaturated precursors of the cyclopropane mycolates were commonly encountered. Among unusual α-mycolates, many strains had tricyclopropyl components with chains extended by 6 to 8 carbons. Significantly, (Canetti) and had α-mycolates with a double bond and cyclopropane ring, whose chain lengths suggested a relationship to possible precursors of oxygenated mycolates. The methoxy- and ketomycolates from a majority of strains had minor amounts of components with additional cyclopropane rings, some of whose chains were also extended by 6 to 8 carbons. These latter mycolates were major components in the attenuated H37Ra strain, whose mycolate profile was distinct from those of other strains of

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2001-07-01
2024-03-28
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References

  1. Brennan P. J., Nikaido H. 1995; The envelope of mycobacteria. Annu Rev Biochem 64:29–63 [CrossRef]
    [Google Scholar]
  2. Daffé M. Draper P. 1998; The envelope layers of mycobacteria with reference to their pathogenicity. Adv Microb Physiol 39:131–203
    [Google Scholar]
  3. 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
    [Google Scholar]
  4. Draper P. 1998; The outer parts of the mycobacterial envelope as permeability barriers. Front Biosci 3:1253–1261
    [Google Scholar]
  5. Dubnau E., Soares S., Benichou A., Vaz T, Lanéelle M. A., 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 [CrossRef]
    [Google Scholar]
  6. Hamid M. E., Minnikin D. E., Goodfellow M. 1993; A simple chemical test to distinguish mycobacteria from other mycolic acid-containing actinomycetes. J Gen Microbiol 139:2203–2213 [CrossRef]
    [Google Scholar]
  7. Hashimoto N., Aoyama T., Shioiri T. 1981; New methods and reagents in organic synthesis 14. A simple efficient preparation of methyl esters with trimethylsilyldiazomethane (TMSCHN2) and its application to gas chromatographic analysis of fatty acids. Chem Pharm Bull 29:1475–1478 [CrossRef]
    [Google Scholar]
  8. Jenkins I. D., Goren M. B. 1986; Improved synthesis of cord factor analogues via the Mitsunobu reaction. Chem Phys Lipids 41:225–235 [CrossRef]
    [Google Scholar]
  9. Kremer L., Baulard A. R., Besra G. S. 2000; Genetics of mycolic acid biosynthesis. In Molecular Genetics of Mycobacteria pp 173–190 Edited by Hatfull G. F., Jacobs W. R. Jr Washington DC: American Society for Microbiology;
    [Google Scholar]
  10. McNeil M. R., Brennan P. J. 1991; Structure, function and biogenesis of the cell envelope of mycobacteria in relation to bacterial physiology, pathogenesis and drug resistance: some thoughts and possibilities arising from recent structural information. Res Microbiol 7th Forum 142:451–463
    [Google Scholar]
  11. McNeil M. R., Brennan P. J, Daffé M. 1991; Locations of the mycolyl ester substituents in the cell wall of mycobacteria. J Biol Chem 266:13217–13223
    [Google Scholar]
  12. Minnikin D. E. 1991; Chemical principles in the organization of lipid components in the mycobacterial cell envelope. Res Microbiol 7th Forum 142:423–427
    [Google Scholar]
  13. Minnikin D. E., Polgar N. 1967; Mycolic acids from human and avian tubercle bacilli. Chem Commun916–918
    [Google Scholar]
  14. Minnikin D. E., Minnikin S. M., Parlett J. H., Goodfellow M., Magnusson M. 1984a; Mycolic acid patterns of some species of Mycobacterium . Arch Microbiol 139:225–231
    [Google Scholar]
  15. Minnikin D. E., Parlett J. H., Magnusson M., Ridell M., Lind A. 1984b; Mycolic acid patterns of representatives of Mycobacterium bovis BCG. J Gen Microbiol 130:2733–2736
    [Google Scholar]
  16. Minnikin D. E., Parlett J. H., Dobson G., Goodfellow M., Magnusson M., Ridell M. 1986; Lipid profiles of members of the Mycobacterium tuberculosis complex. In Mycobacteria of Clinical Interest pp 75–78 Edited by Casal M. Amsterdam: Elsevier;
    [Google Scholar]
  17. Paul T. R., Beveridge T. J. 1992; Re-evaluation of envelope profiles and cytoplasmic ultrastructure of mycobacteria processed by conventional embedding and freeze-substitution protocols. J Bacteriol 174:6508–6517
    [Google Scholar]
  18. Paul T. R., Beveridge T. J. 1994; Preservation of surface lipids and determination of ultrastructure of Mycobacterium kansasii by freeze-substitution. Infect Immun 62:1542–1555
    [Google Scholar]
  19. Qureshi N., Takayama K., Jordi H. C., Schnoes H. K. 1978; Characterization of the purified components of a new homologous series of alpha-mycolic acids from Mycobacterium tuberculosis H37Ra. J Biol Chem 253:5411–5417
    [Google Scholar]
  20. Takayama K., Qureshi N., Jordi H. C., Schnoes H. K. 1979; Separation of homologous series of mycolic acids from Mycobacterium tuberculosis H37Ra by high performance liquid chromatography. In Biological/Biomedical Applications of Liquid Chromatography pp 91–101 Edited by Hawk G. L. New York: Marcel Dekker;
    [Google Scholar]
  21. Watanabe M., Yamada Y., Iguchi K., Minnikin D. E. 1994; Structural elucidation of new phenolic glycolipids from Mycobacterium tuberculosis . Biochim Biophys Acta 1210:174–180 [CrossRef]
    [Google Scholar]
  22. Watanabe M., Ohta A., Sasaki S., Minnikin D. E. 1999; Structure of a new glycolipid from the Mycobacterium avium–Mycobacterium intracellulare complex. J Bacteriol 181:2293–2297
    [Google Scholar]
  23. Yuan Y., Barry C. E.III. 1996; A common mechanism for the biosynthesis of methoxy and cyclopropyl mycolic acids in Mycobacterium tuberculosis . Proc Natl Acad Sci USA 93:12828–12833 [CrossRef]
    [Google Scholar]
  24. Yuan Y., Crane D. C., Musser J. M., Sreevatsan S., Barry C. E.III. 1997; MMAS-1, the branch point between cis - and trans -cyclopropane-containing oxygenated mycolates in Mycobacterium tuberculosis. J Biol Chem 272:10041–10049 [CrossRef]
    [Google Scholar]
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