Absolute configuration of the unique 2,6-dideoxy-4-O-methyl-arabino-hexopyranose of the major phenolic glycolipid antigen from Mycobacterium kansasii

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Abstract
The antigenicity and the structure of the major phenolic glycolipid from Mycobacterium kansasii have been established. A monoacetylated tetrasaccharide structure was proposed for the oligosaccharide moiety in which the distal sugar, unique in nature, corresponds to 2,6‐dideoxy‐4‐O‐methyl‐α‐arabinohexopyranose. Its terminal position in the oligosaccharide part confers to this residue a key role in the antigen‐antibody interaction. By improvement of the methanolysis procedure, this new kind of sugar was obtained in higher amounts than by hydrolysis of the glycolipid. Its 1H‐NMR spectrum is presented and its optical rotatory power measurement agrees with a d absolute configuration while the deoxyhexoses involved in the glycolipid tetrasaccharide structure present the l absolute configuration.