N-acylkansosamine. A novel N-acylamino sugar from the trehalose-containing lipooligosaccharide antigens of Mycobacterium kansasii.

作者: S W Hunter , T Fujiwara , R C Murphy , P J Brennan

DOI: 10.1016/S0021-9258(17)42760-8

关键词: Reducing sugarMycobacterium kansasiiTrehaloseChemistryChemical ionizationNuclear magnetic resonance spectroscopyOrganic chemistryMass spectrometryCarbon-13 NMRSugar

摘要: A novel N-acylamino sugar was isolated from the antigenic trehalose-containing lipooligosaccharides IV-VII of Mycobacterium kansasii. The native reducing sugar, its O-acetyl derivative, methylglycoside, O-acetylated alditol, and de-N-acylated N-, alditol were all examined by high resolution 1H NMR, 13C direct probe gas-liquid chromatography-mass spectrometry in both chemical ionization electron impact modes, mass spectrometry. dideoxy had a formula weight 277, an empirical C12H23NO6, C- O-methyl substituents, N-methoxypropionyl branch. Upon alkaline hydrolysis, methoxypropionic acid released shown to correspond synthetic compound gas chromatography structure 4,6-dideoxy-2-O-methyl-3-C-methyl-4-(2'-methoxypropionamido)-alpha beta-L-manno-hexopyranose, with trivial name N-acylkansosamine, is proposed. present more polar, highly regarded as exclusive M. kansasii primary cell wall immunodeterminant.

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