Structure of the specific oligosaccharides from the glycopeptidolipid antigens of serovars in the Mycobacterium avium-Mycobacterium intracellulare-Mycobacterium scrofulaceum complex. 1981

P J Brennan, and G O Aspinall, and J E Shin

The specific oligosaccharide units of the C-mycosidic glycopeptidolipid antigens from serovarieties in the Myobacterium avium-Mycobacterium intracellulare-Mycobacterium scrofulaceum complex were liberated as oligosaccharide alditols by treatment of the glycopeptidolipids with alkaline borohydride. The complete structures of the oligosaccharide alditols have been derived from their 1H-NMR spectra or those of their permethylated (or pertrideuteriomethylated) derivatives, the mass spectra of the methylated derivatives, and from methylation fragmentation analysis. Periodate oxidation was also used to confirm the position of the link between the ultimate and penultimate sugars. The following structures are proposed (with some extrapolation of enantiomeric configurations where evidence for assignment is not yet complete) for the oligosaccharide alditols: Serovar 9 2,3-Me2-alpha-L-Fucp-(1 leads to 4)-2,3-Me2-alpha-L-Fucp-(1 leads to 3)-alpha-L-Rhap-(1 leads to 2)-6-deoxy-L-Talol Serovar 25 2-Me-alpha-L-Fucp-(1 leads to 4)-2-Me-alpha-L-Fucp-(1 leads to 3)-alpha-L-Rhap-(1 leads to 2)-6-deoxy-L-talol Serovar 8 4,6-(1'-carboxyethylidene)-3-Me-beta-D-Glcp-(1 leads to 3)-alpha-L-Rhap-(1 leads to 2)-6-deoxy-L-Talol Thus, 6-deoxytalitol (6-deoxytalose in the original glycopeptidolipid) invariably occupies the reducing terminus. Rhamnose is invariably the penultimate sugar, and the link between rhamnose and 6-deoxytalose is invariably alpha 1 leads to 2. Moreover, the results point to the outer one or two appendages for the provision of individually distinctive features required for antigen specificity. The abbreviations used are: serovar, serologically distinct varieties; Me, methyl; Fucp, fucopyranose; Rhap, rhamnopyranose; Talol, talitol.

UI MeSH Term Description Entries
D008074 Lipoproteins Lipid-protein complexes involved in the transportation and metabolism of lipids in the body. They are spherical particles consisting of a hydrophobic core of TRIGLYCERIDES and CHOLESTEROL ESTERS surrounded by a layer of hydrophilic free CHOLESTEROL; PHOSPHOLIPIDS; and APOLIPOPROTEINS. Lipoproteins are classified by their varying buoyant density and sizes. Circulating Lipoproteins,Lipoprotein,Lipoproteins, Circulating
D009161 Mycobacterium A genus of gram-positive, aerobic bacteria. Most species are free-living in soil and water, but the major habitat for some is the diseased tissue of warm-blooded hosts. Mycobacteria
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D009844 Oligosaccharides Carbohydrates consisting of between two (DISACCHARIDES) and ten MONOSACCHARIDES connected by either an alpha- or beta-glycosidic link. They are found throughout nature in both the free and bound form. Oligosaccharide
D002236 Carbohydrate Conformation The characteristic 3-dimensional shape of a carbohydrate. Carbohydrate Linkage,Carbohydrate Conformations,Carbohydrate Linkages,Conformation, Carbohydrate,Conformations, Carbohydrate,Linkage, Carbohydrate,Linkages, Carbohydrate
D002240 Carbohydrate Sequence The sequence of carbohydrates within POLYSACCHARIDES; GLYCOPROTEINS; and GLYCOLIPIDS. Carbohydrate Sequences,Sequence, Carbohydrate,Sequences, Carbohydrate
D006020 Glycopeptides Proteins which contain carbohydrate groups attached covalently to the polypeptide chain. The protein moiety is the predominant group with the carbohydrate making up only a small percentage of the total weight. Glycopeptide
D000942 Antigens, Bacterial Substances elaborated by bacteria that have antigenic activity. Bacterial Antigen,Bacterial Antigens,Antigen, Bacterial
D013045 Species Specificity The restriction of a characteristic behavior, anatomical structure or physical system, such as immune response; metabolic response, or gene or gene variant to the members of one species. It refers to that property which differentiates one species from another but it is also used for phylogenetic levels higher or lower than the species. Species Specificities,Specificities, Species,Specificity, Species
D013058 Mass Spectrometry An analytical method used in determining the identity of a chemical based on its mass using mass analyzers/mass spectrometers. Mass Spectroscopy,Spectrometry, Mass,Spectroscopy, Mass,Spectrum Analysis, Mass,Analysis, Mass Spectrum,Mass Spectrum Analysis,Analyses, Mass Spectrum,Mass Spectrum Analyses,Spectrum Analyses, Mass

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