title: Synthesis of an unusual polar glycopeptidolipid in glucose-limited culture of Mycobacterium smegmatis.
abstract: 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 beta-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.
mesh_terms: D003470:Culture Media; D005947:Glucose / Q000378:metabolism; D006017:Glycolipids / Q000302:isolation & purification / Q000378:metabolism*; D020102:Mycobacterium smegmatis / Q000254:growth & development* / Q000378:metabolism; D010455:Peptides / Q000302:isolation & purification / Q000378:metabolism*; D021241:Spectrometry, Mass, Electrospray Ionization; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D003470:Culture Media; D006017:Glycolipids; D010455:Peptides; D005947:Glucose