There has been a general understanding that Mycobacterium smegmatis produces only apolar glycopeptidolipid (GPL), similar in structure to serovar non-specific GPL of Mycobacterium avium. In this study, synthesis of polar GPL in carbon-starved M. smegmatis is reported. Mass spectrometric analysis suggests the polar GPL to be a hyperglycosylated species. The earlier structural studies of polar GPLs from M. avium have invariably shown the presence of an oligosaccharide appendage to D-allo-Thr. However, a further chemical analysis using β-elimination of the newly found polar GPL in M. smegmatis shows that the molecule still contains a monosaccharide at the D-allo-Thr, thus suggesting a new form of polar GPL.
AspinallG. O,
ChatterjeeD.,
BrennanP. J.
1995; The variable surface glycolipids of mycobacteria: structures, synthesis of epitopes, and biological properties. Adv Carbohydr Chem Biochem 51:169–242
BelisleJ. T,
PascopellaL,
InamineJ. M,
BrennanP. J.,
JacobsW. R.Jr1991; Isolation and expression of a gene cluster responsible for biosynthesis of the glycopeptidolipid antigens of Mycobacterium avium
. J Bacteriol 173:6991–6997
BelisleJ. T,
McNeilM. R,
ChattejeeD,
InamineJ. M.,
BrennanP. J.
1993; Expression of the core lipopeptide of the glycopeptidolipid surface antigens in rough mutants of Mycobacterium avium
. J Biol Chem 268:10510–10516
Billman-JacobeH,
McConvilleM. J,
HaitesR. E,
KovacevicS.,
CoppelR. L.
1999; Identification of a peptide synthetase involved in the biosynthesis of glycopeptidolipids of Mycobacterium smegmatis
. Mol Microbiol 33:1244–1253
ChenP,
RuizR. E,
LiQ,
SilverR. F.,
BishaiW. R.
2000; Construction and characterization of a Mycobacterium tuberculosis mutant lacking the alternate sigma factor gene, sigF
. Infect Immun 68:5575–5580
DaffeM,
LaneelleM. A.,
PuzoG.
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
McNeilM,
ChatterjeeD,
HunterS. W.,
BrennanP. J.
1989; Mycobacterial glycolipids: isolation, structures, antigenicity, and synthesis of neoantigens. Methods Enzymol 179:215–242
OjhaA. K,
MukherjeeT. K.,
ChatterjiD.
2000; High intracellular level of guanosine tetraphosphate in Mycobacterium smegmatis changes the morphology of the bacterium. Infect Immun 68:4084–4091
PattersonJ. H,
McConvilleM. J,
HaitesR. E,
CoppelR. L.,
Billman-JacobeH.
2000; Identification of a methyltransferase from Mycobacterium smegmatis involved in glycopeptidolipid synthesis. J Biol Chem 275:24900–24906