1887

Abstract

The presence of a polar species of glycopeptidolipid (GPL) in carbon-starved has been reported previously. In this study, the complete structure of this GPL is established with the help of MALDI-TOF (matrix assisted laser desorption/ionization time of flight) and ESI (electrospray ionization) -MS, C-SEFT (spin echo Fourier transform) -NMR spectroscopy, and HPLC analysis. In the molecule, two units of a 3,4-di--methyl derivative of rhamnose are attached to -alaninol via a 1→2 linkage. Various methyl derivatives of rhamnose and 6-deoxytalose were synthesized as standards to establish this structure. The accumulation of this polar GPL in is dependent, as a SigB-overproducing strain of shows the presence of this spot in the exponential phase, and a -knockout strain of does not show the presence of any polar GPLs.

Loading

Article metrics loading...

/content/journal/micro/10.1099/mic.0.27908-0
2005-07-01
2019-08-24
Loading full text...

Full text loading...

/deliver/fulltext/micro/151/7/mic1512385.html?itemId=/content/journal/micro/10.1099/mic.0.27908-0&mimeType=html&fmt=ahah

References

  1. Barrow, W. W., Ullom, B. P. & Brennan, P. J. ( 1980; ). Peptidoglycolipid nature of the superficial cell wall sheath of smooth colony-forming mycobacteria. J Bacteriol 144, 814–822.
    [Google Scholar]
  2. Belisle, J. T. & Brennan, P. J. ( 1989; ). Chemical basis of rough and smooth variation in Mycobacteria. J Bacteriol 171, 3465–3470.
    [Google Scholar]
  3. Belisle, J. T., Pascopella, L., Inamine, J. M., Brennan, P. J. & Jacobs, W. R., Jr ( 1991; ). Isolation and expression of a gene cluster responsible for biosynthesis of the glycopeptidolipid antigens of Mycobacterium avium. J Bacteriol 173, 6991–6997.
    [Google Scholar]
  4. Billman-Jacobe, H. ( 2004; ). Glycopeptidolipid synthesis in mycobacteria. Curr Sci 86, 111–114.
    [Google Scholar]
  5. Billman-Jacobe, H., McConville, M. J., Haites, R. E., Kovacevic, S. & Coppel, R. L. ( 1999; ). Identification of a peptide synthetase involved in the biosynthesis of glycopeptidolipids of Mycobacterium smegmatis. Mol Microbiol 33, 1244–1253.
    [Google Scholar]
  6. Brennan, P. J. & Goren, M. B. ( 1979; ). Structural studies on the type-specific antigens and lipids of the Mycobacterium avium, Mycobacterium intracellulare, Mycobacterium scrofulaceum serocomplex: Mycobacterium intracellulare serotype 9. J Biol Chem 254, 4205–4211.
    [Google Scholar]
  7. Brown, D. W., Nakashima, T. T. & Rabenstein, D. L. ( 1981; ). Simplification and assignment of carbon-13 NMR spectra with spin-echo Fourier transform techniques. J Magn Reson 45, 302–314.
    [Google Scholar]
  8. Daffé, M., Lanéelle, M. A. & Puzo, G. ( 1983; ). Structural elucidation by field desorption and electron-impact mass spectrometry of the C-mycosides isolated from Mycobacterium smegmatis. Biochim Biophys Acta 751, 439–443.[CrossRef]
    [Google Scholar]
  9. Eckstein, T. M., Cilbaq, F. S., Chatterjee, D., Kelly, N. J., Brennan, P. J. & Belisle, J. T. ( 1998; ). Identification and recombinant expression of a Mycobacterium avium rhamnosyltransferase gene (rtfA) involved in glycopeptidolipid biosynthesis. J Bacteriol 180, 5567–5573.
    [Google Scholar]
  10. Jeevarajah, D., Patterson, J. H., McConville, M. J. & Billman-Jacobe, H. ( 2002; ). Modification of glycopeptidolipids by an O-methyltransferase of Mycobacterium smegmatis. Microbiology 148, 3079–3087.
    [Google Scholar]
  11. Jeevarajah, D., Patterson, J. H., Taig, E., Sargeant, T., McConville, M. J. & Billman-Jacobe, H. ( 2004; ). Methylation of GPLs in Mycobacterium smegmatis and Mycobacterium avium. J Bacteriol 186, 6792–6799.[CrossRef]
    [Google Scholar]
  12. Khoo, K. H., Jarboe, E., Barker, A., Torrelles, J., Kuo, C. W. & Chatterjee, D. ( 1999; ). Altered expression profile of the surface glycopeptidolipids in drug-resistant clinical isolates of Mycobacterium avium complex. J Biol Chem 274, 9778–9785.[CrossRef]
    [Google Scholar]
  13. Maslow, J. N., Irani, V. R., Lee, S.-H., Eckstein, T. M., Inamine, J. M. & Belisle, J. T. ( 2003; ). Biosynthetic specificity of the rhamnosyltransferase gene of Mycobacterium avium serovar 2 as determined by allelic exchange mutagenesis. Microbiology 149, 3193–3202.[CrossRef]
    [Google Scholar]
  14. Mechref, Y., Krishnan, C. & Novotny, M. V. ( 2003; ). Structural characterization of oligosaccharides using MALDI-TOF/TOF tandem mass spectrometry. Anal Chem 75, 4895–4903.[CrossRef]
    [Google Scholar]
  15. Nyka, W. ( 1974; ). Studies on the effect of starvation on mycobacteria. Infect Immun 9, 843–850.
    [Google Scholar]
  16. Ojha, A. K., Mukherjee, T. K. & Chatterji, D. ( 2000; ). High intracellular level of guanosine tetraphosphate in Mycobacterium smegmatis changes the morphology of the bacterium. Infect Immun 68, 4084–4091.[CrossRef]
    [Google Scholar]
  17. Ojha, A. K., Varma, S. & Chatterji, D. ( 2002; ). Synthesis of an unusual polar glycopeptidolipid in glucose-limited culture of Mycobacterium smegmatis. Microbiology 148, 3039–3048.
    [Google Scholar]
  18. Ortalo-Magné, A., Lemassu, A., Lanéelle, M. A., Bardou, F., Silve, G., Gounon, P., Marchal, G. & Daffé, M. ( 1996; ). Identification of the surface-exposed lipids on the cell envelopes of Mycobacterium tuberculosis and other mycobacterial species. J Bacteriol 178, 456–461.
    [Google Scholar]
  19. Patterson, J. H., McConville, M. J., Haites, R. E., Coppel, R. L. & Billman-Jacobe, H. ( 2000; ). Identification of a methyltransferase from Mycobacterium smegmatis involved in glycopeptidolipid synthesis. J Biol Chem 275, 24900–24906.[CrossRef]
    [Google Scholar]
  20. Pozsgay, V., Nanasi, P. & Neszmelyi, A. ( 1981; ). Synthesis, and carbon-13 study, of O-α-l-rhamnopyranosyl-(1→3)-o-α-l-rhamnopyranosyl-(1→2)-l-rhamnopyranose and o-α-l-rhamnopyranosyl-(1→3)-o-α-l-rhamnopyranosyl-(1→3)-l-rhamnopyranose, constituents of bacterial cell wall polysaccharides. Carbohydr Res 90, 215–231.[CrossRef]
    [Google Scholar]
  21. Riviere, M. & Puzo, G. ( 1991; ). A new type of serine-containing glycopeptidolipid from Mycobacterium xenopi. J Biol Chem 266, 9057–9063.
    [Google Scholar]
  22. Snapper, S. B., Melton, R. E., Mustafa, S., Kieser, T. & Jacobs, W. R., Jr ( 1990; ). Isolation and characterization of efficient plasmid transformation mutants of Mycobacterium smegmatis. Mol Microbiol 4, 1911–1919.[CrossRef]
    [Google Scholar]
  23. Stover, C. K., de la Cruz, V. F., Fuerst, T. R. & 11 other authors ( 1991; ). New use of BCG for recombinant vaccines. Nature 351, 456–460.[CrossRef]
    [Google Scholar]
  24. Villeneuve, C., Etienne, G., Abadie, V., Montrozier, H., Bordier, C., Laval, F., Daffé, M., Maridonneauparini, I. & Astarie-Dequeker, C. ( 2003; ). Surface exposed glycopeptidolipids of Mycobacterium smegmatis specifically inhibit the phagocytosis of mycobacteria by human macrophages. Identification of a novel family of glycopeptidolipid. J Biol Chem 278, 51291–51300.[CrossRef]
    [Google Scholar]
http://instance.metastore.ingenta.com/content/journal/micro/10.1099/mic.0.27908-0
Loading
/content/journal/micro/10.1099/mic.0.27908-0
Loading

Data & Media loading...

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