Demonstration that the galactosyl and arabinosyl residues in the cell-wall arabinogalactan of Mycobacterium leprae and Myobacterium tuberculosis are furanoid

Carbohydrate Research
1987.0

Abstract

By a complex process involving methylation, partial hydrolysis with acid, reduction with sodium borodeuteride, ethylation, further hydrolysis and reduction, and subsequent capillary gas-liquid chromatography-mass spectrometry of the derived alditol acetates, it was established that the arabinogalactans of Mycobacterium leprae and Mycobacterium tuberculosis contain arabinofuranyosyl and galactofuranosyl residues exclusively. Thus, the covalently bound, highly immunogenic arabinogalactan of mycobacteria, and presumably of other actinomycetes, is highly unusual, in that all of the glycosyl residues are in the furanoid form. Furthermore, by establishing that the galactofuranosyl residues are either 5-, 6-, or 5,6-linked, their linkage pattern was established, and the literature is corrected on this point.

Knowledge Graph

Similar Paper

Demonstration that the galactosyl and arabinosyl residues in the cell-wall arabinogalactan of Mycobacterium leprae and Myobacterium tuberculosis are furanoid
Carbohydrate Research 1987.0
Synthesis of arabinose glycosyl sulfamides as potential inhibitors of mycobacterial cell wall biosynthesis
European Journal of Medicinal Chemistry 2015.0
Synthesis of methyl 5-S-alkyl-5-thio-d-arabinofuranosides and evaluation of their antimycobacterial activity
Bioorganic & Medicinal Chemistry 2008.0
Synthesis of symmetrical C- and pseudo-symmetrical O-linked disaccharide analogs for arabinosyltransferase inhibitory activity in Mycobacterium tuberculosis
Bioorganic & Medicinal Chemistry Letters 2007.0
Synthesis and screening of ( E )-1-(β- d -galactopyranosyl)-4-(aryl)but-3-ene-2-one against Mycobacterium tuberculosis
Bioorganic & Medicinal Chemistry Letters 2011.0
Formation of<i>β</i>-Galactosyl Compounds of Arabinosylcytosine in Growing Culture of<i>Sporobolomyces singularis</i>
Bioscience, Biotechnology, and Biochemistry 1994.0
Synthesis of Arabino glycosyl triazoles as potential inhibitors of mycobacterial cell wall biosynthesis
Bioorganic &amp; Medicinal Chemistry Letters 2008.0
Structural features of cell-wall polysaccharides of the carrot Daucus carota
Carbohydrate Research 1984.0
Isolation and structure of mycobactin T, a growth factor from <i>Mycobacterium tuberculosis</i>
Biochemical Journal 1965.0
The Arabinosyltransferase EmbC Is Inhibited by Ethambutol in Mycobacterium tuberculosis
Antimicrobial Agents and Chemotherapy 2009.0