1887

Abstract

SUMMARY: Trehalose-6-monomycolate (TMM) was isolated from the lipids of armadillo-derived Only meagre amounts of this glycolipid were recovered, but its structure was unequivocally established. Only α-mycolates were detected in the TMM by Cf plasma desorption mass spectrometry. Electron impact mass spectrometry showed the alpha branch to be principally C. Trehalose dimycolate (cord factor) was not detectable. Since we have also found TMM in and in every species so far examined, we suggest that this glycolipid is truly ubiquitous amongst mycobacteria.

Loading

Article metrics loading...

/content/journal/micro/10.1099/00221287-133-1-201
1987-01-01
2022-01-18
Loading full text...

Full text loading...

/deliver/fulltext/micro/133/1/mic-133-1-201.html?itemId=/content/journal/micro/10.1099/00221287-133-1-201&mimeType=html&fmt=ahah

References

  1. Ahibo-Coffy A., Aurelle H., Lacave C., Promé J. C., Puzo G., Savagnac A. 1978; Isolation, structural studies and chemical synthesis of a palmitone lipid from Corynebacterium diphtheriae. Chemistry and Physics of Lipids 22:185–195
    [Google Scholar]
  2. Arnarp J., Lönngren J. 1978; Alkylation of carbohydrates with alkyl trifluoromethanesulfonates. Acta chemica Scandinavia B32:465–467
    [Google Scholar]
  3. Asselineau C., Asselineau J. 1978; Trehalose-containing glycolipids. Progress in the Chemistry of Fats and Other Lipids 16:59–99
    [Google Scholar]
  4. Asselineau C., Clavel S., Clément F., Daffé M., David H., Lanéèlle M. A., Promé J. C. 1981; Constituants lipidiques de Mycobacterium leprae isole de tatou infecté experimentalement. Annales de microbiologie 132A:19–30
    [Google Scholar]
  5. Azuma S., Yamamura Y. 1963; Studies on the firmly bound lipids of human tubercle bacillus. II. Isolation of arabinose mycolate and identification of its chemical structure. Journal of Biochemistry 53:275–281
    [Google Scholar]
  6. Bruneteau M., Michel G. 1968; Structure d’un dimycolate d’arabinose isolé de Mycobacterium marianum. Chemistry and Physics of Lipids 2:229–239
    [Google Scholar]
  7. Davidson L. A., Draper P., Minnikin D. E. 1982; Studies on the mycolic acids from the walls of Mycobacterium microti. Journal of General Microbiology 128:823–828
    [Google Scholar]
  8. Dhariwal K. R., Dhariwal G., Goren M. B. 1984; Observations on the ubiquity of the Mycobacterium tuberculosis sulfatides in mycobacteria. American Review of Respiratory Diseases 130:641–646
    [Google Scholar]
  9. Draper P. 1976; Cell walls of Mycobacterium leprae. International Journal of Leprosy 44:95–98
    [Google Scholar]
  10. Draper P. 1979; Annex 1, protocol 1/79. Report of the enlarged supervisory council meeting for research on the immunology of leprosy. Geneva: World Health Organization;
    [Google Scholar]
  11. Draper P., Rees R. J. W. 1973; The nature of the electron-transparent zone that surrounds Mycobacterium lepraemurium inside host cells. Journal of General Microbiology 77:79–87
    [Google Scholar]
  12. Draper P., Dobson G., Minnikin D. E., Minnikin S. M. 1982; The mycolic acids of Mycobacterium leprae harvested from experimentally infected nine-banded armadillos. Annales de microbiologie 133B:39–47
    [Google Scholar]
  13. Etemadi A. H. 1967; The use of pyrolysis gas chromatography and mass spectroscopy in the study of the structure of mycolic acids. Journal of Gas Chromatography 5:447–456
    [Google Scholar]
  14. Folch J., Lees M., Sloane-Stanley G. H. 1957; A simple method for isolation and purification of total lipids from animal tissues. Journal of Biological Chemistry 226:497–509
    [Google Scholar]
  15. Gastambide-Odier M., Lederer E. 1964; Biosynthesis of corynomycolic acid from two molecules of palmitic acid. Nature; London: 1841563–1564
    [Google Scholar]
  16. Gastambide-Odier M., Delaumeny J. M., Lederer E. 1964; Mise en évidence de cycles propaniques dans divers acides mycoliques de souche humaines et bovines de Mycobacterium tuberculosis. Comptes rendus hebdomadaires des seances de l’Académie des sciences 259:3404–3407
    [Google Scholar]
  17. Goren M. B. 1970a; Sulfolipid I of Mycobacterium tuberculosis, strain H37Rv. I. Purification and properties. Biochimica et biophysica acta 210:116–126
    [Google Scholar]
  18. Goren M. B. 1970b; Sulfolipid I of Mycobacterium tuberculosis, strain H37Rv. II. Structural studies. Biochimica et biophysica acta 210:127–138
    [Google Scholar]
  19. Goren M. B., Brennan P. J. 1979; Mycobacterial lipids: chemistry and biologic activities. In Tuberculosis pp. 63–193 Youmans G. P. Edited by Philadelphia: W. B. Saunders;
    [Google Scholar]
  20. Goren M. B., Brokl O. 1974; Separation and purification of cord factor (6,6′-dimycoloyl trehalose) from wax C or from mycolic acids. Recent Results in Cancer Research 47:251–258
    [Google Scholar]
  21. Goren M. B., Brokl O., Roller P., Fales H. M., Das B. C. 1976; Sulfatides of Mycobacterium tuberculosis: the structure of the principal sulfatide (SL-I). Biochemistry 15:2728–2734
    [Google Scholar]
  22. Goren M. B., Brokl O., Roller P. 1979; Cord factor (trehalose-6,6′-dimycolate) of in vivo-derived Mycobacterium lepraemurium. Biochimica et biophysica acta 574:70–78
    [Google Scholar]
  23. Hunter S. W., Brennan P. J. 1981; A novel phenolic glycolipid from Mycobacterium leprae possibly involved in immunogenicity and pathogenicity. Journal of Bacteriology 147:728–735
    [Google Scholar]
  24. Kanetsuna F., Imaeda T., Cunto G. 1969; On the linkage between mycolic acid and arabinogalactan in phenol treated mycobacterial cell walls. Biochimica et biophysica acta 173:341–344
    [Google Scholar]
  25. Kato M., Maeda J. 1974; Isolation and biochemical activities of trehalose-6-monomycolate of Mycobacterium tuberculosis. Infection and Immunity 9:814
    [Google Scholar]
  26. Kilburn J. O., Takayama K., Armstrong E. L. 1982; Synthesis of trehalose dimycolate (cord factor) by a cell-free system of Mycobacterium smegmatis. Biochemical and Biophysical Research Communications 108:132–139
    [Google Scholar]
  27. Kusaka T., Kohsaka K., Fukunishi Y., Akimori H. 1981; Isolation and identification of mycolic acids in Mycobacterium leprae and Mycobacterium lepraemurium. International Journal of Leprosy 49:406–416
    [Google Scholar]
  28. Lederer E. 1976; Cord factor and related trehalose esters. Chemistry and Physics of Lipids 16:91–106
    [Google Scholar]
  29. Lederer E. 1984; Chemistry of mycobacterial cord-factor and related natural and synthetic trehalose esters. In The Mycobacteria. A Source Book 1 pp. 361–378 Kubica G. P., Wayne L. G. Edited by New York: Marcel Dekker;
    [Google Scholar]
  30. Liav A., Goren M. B. 1980; A new synthesis of cord factor and analogs. Chemistry and Physics of Lipids 27:345–352
    [Google Scholar]
  31. Liav A., Goren M. B. 1984; Synthesis of 6-O-mycoloyl-and 6-O-corynomycoloyl-±,±-trehalose. Carbohydrate Research 125:323–328
    [Google Scholar]
  32. Liav A., Goren M. B. 1986; An improved synthesis of 6-O-mycoloyl-and 6-O-corynomycoloyl-±,±-trehalose with observations on the permethyla-tion analysis of trehalose glycolipids. Carbohydrate Research 154: in the Press
    [Google Scholar]
  33. Macfarlane R. D. 1983; Californium-252 plasma desorption mass spectrometry. Analytical Chemistry 55:1247A–1264A
    [Google Scholar]
  34. Minnikin D. E. 1982; Lipids: complex lipids, their chemistry, biosynthesis and roles. In The Biology of the Mycobacteria 1 pp. 95–184 Ratledge C., Stanford J. Edited by London: Academic Press;
    [Google Scholar]
  35. Minnikin D. E., Dobson G., Draper P. 1985; The free lipids of Mycobacterium leprae harvested from experimentally infected nine-banded armadillos. Journal of General Microbiology 131:2007–2011
    [Google Scholar]
  36. Nakamura M., Itoh T., Yoshitake Y., Sengupta U., Goren M. B. 1984; Biochemical characteristics of M. lepraemurium propagated in cell-free liquid medium. International Journal of Leprosy 52: supplement no. 4 720
    [Google Scholar]
  37. Noll H., Bloch H. 1955; Studies on the chemistry of the cord factor of Mycobacterium tuberculosis. Journal of Biological Chemistry 214:251–265
    [Google Scholar]
  38. Noll H., Bloch H., Asselineau J., Lederer E. 1956; The chemical structure of the cord factor of Mycobacterium tuberculosis. Biochimica et biophysica acta 20:299–309
    [Google Scholar]
  39. Promé J. C., Walker R. W., Lacave C. 1974; Condensation de deux molécules d’acide palmitique chez Corynebacterium diphtheriae: formation d’un β-ceto ester de tréhalose. Comptes rendus hebdomadaires des séances de l’Académie de sciences C218:1065–1068
    [Google Scholar]
  40. Takayama K., Armstrong E. L. 1976; Isolation, characterization and function of 6-mycoloyl-6′-acetyltrehalose in the H37Ra strain of Mycobacterium tuberculosis. Biochemistry 15:441–447
    [Google Scholar]
  41. Takayama K., Qureshi N. 1984; Structure and synthesis of lipids. In The Mycobacteria. A Source Book 1 pp. 361–378 Kubica G. P., Wayne L. G. Edited by New York: Marcel Dekker;
    [Google Scholar]
  42. Vilkas E., Markovits J. 1968; Isolement d’un digalactoside et d’un mycolate de diarabinoside a partir de cires D d’une souche humaine virulente de Mycobacterium tuberculosis. FEBS Letters 2:20–22
    [Google Scholar]
  43. Walker R. W., Promé J. C., Lacave C. 1973; Biosynthesis of mycolic acids. Formation of a C32β-keto ester from palmitic acid in a cell-free system of Corynebacterium diphtheriae. Biochimica et biophysica acta 326:52–62
    [Google Scholar]
http://instance.metastore.ingenta.com/content/journal/micro/10.1099/00221287-133-1-201
Loading
/content/journal/micro/10.1099/00221287-133-1-201
Loading

Data & Media loading...

Most cited this month Most Cited RSS feed

This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error