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

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 12 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.

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