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Microbiology 151 (2005), 2385-2392; DOI  10.1099/mic.0.27908-0
© 2005 Society for General Microbiology

Hyperglycosylation of glycopeptidolipid of Mycobacterium smegmatis under nutrient starvation: structural studies

Raju Mukherjee1, Manuel Gomez2, Narayanaswamy Jayaraman3, Issar Smith2 and Dipankar Chatterji1

1 Molecular Biophysics Unit, Indian Institute of Science, Bangalore-560012, India
2 TB Center, The Public Health Research Institute at the International Center for Public Health, 225 Warren Street, Newark, NJ 07103-3535, USA
3 Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012, India

Correspondence
Dipankar Chatterji
dipankar{at}mbu.iisc.ernet.in

The presence of a polar species of glycopeptidolipid (GPL) in carbon-starved Mycobacterium smegmatis 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, 13C-SEFT (spin echo Fourier transform) -NMR spectroscopy, and HPLC analysis. In the molecule, two units of a 3,4-di-O-methyl derivative of rhamnose are attached to L-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 M. smegmatis is sigB dependent, as a SigB-overproducing strain of M. smegmatis shows the presence of this spot in the exponential phase, and a sigB-knockout strain of M. smegmatis does not show the presence of any polar GPLs.

Abbreviations: a.m.u., atomic mass unit; ESI, electrospray ionization; GPL, glycopeptidolipid; MALDI-TOF, matrix assisted laser desorption/ionization time of flight; MS-MS, tandem mass spectrometry; nsGPL, serovar-nonspecific GPL; SEFT, spin echo Fourier transform; ssGPL, serovar-specific polar GPL




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