title: Structural elucidation of the major phenolic glycolipid from Mycobacterium kansasii. II. Presence of a novel dideoxyhexose.
abstract: A novel O-methyl-2,6-dideoxyhexose was isolated from the major phenolic glycolipid (previously called mycoside A) of Mycobacterium kansasii. Its molecular weight (162) was determined by gas chromatography-mass spectrometry analysis (chemical ionization with ammonia as reactant gas) of its underivatized reducing form. The methoxyl group was located by electron impact-mass spectrometry of its alditol acetate. The configuration was established by 1H NMR of its peracetylated derivative. The structure 2,6-dideoxy-4-O-methyl-arabino-hexopyranose is proposed for this new sugar. Evidence is also presented that the phenolic glycolipid previously called mycoside A is an antigen of M. kansasii since it reacts with rabbit antisera raised against whole M. kansasii.
mesh_terms: D000942:Antigens, Bacterial; D002236:Carbohydrate Conformation; D055598:Chemical Phenomena; D002621:Chemistry; D003837:Deoxy Sugars / Q000302:isolation & purification*; D008401:Gas Chromatography-Mass Spectrometry; D006017:Glycolipids / Q000032:analysis*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008970:Molecular Weight; D009161:Mycobacterium / Q000032:analysis*; D009170:Nontuberculous Mycobacteria / Q000032:analysis*
chemical_list: D000942:Antigens, Bacterial; D003837:Deoxy Sugars; D006017:Glycolipids; C051618:mycoside A; C051619:2,6-dideoxy-4-O-methylhexopyranose