title: Thin-layer chromatography and mass spectrometry of pentafluorobenzylidene derivatives of members of the phthiocerol family from Mycobacterium tuberculosis and Mycobacterium marinum.
abstract: The difference in relative stereochemistry of the 1.3-diol unit of mycobacterial phthiocerols can be determined by simple thin-layer chromatographic analysis of pentafluorobenzylidene acetal derivatives. The threo phthiocerol acetals from Mycobacterium tuberculosis are composed of equal amounts of two axial-equatorial stereoisomers but the erythro phthiocerols from Mycobacterium marinum form only one acetal with diequatorial substituents. The two acetals formed from a threo phthiocerol can be separated by thin-layer chromatography and mass spectra of the two stereoisomers allowed assignment of their structures.
authors.affiliation: Department of Chemistry, University of Newcastle, Newcastle upon Tyne, UK.
authors.forename: S
authors.initials: S
authors.lastname: Hartmann
authors.forename: A I
authors.initials: AI
authors.lastname: Mallet
authors.forename: D E
authors.initials: DE
authors.lastname: Minnikin
authors.forename: M
authors.initials: M
authors.lastname: Ridell
mesh_terms: D000080:Acetals / Q000737:chemistry; D001597:Benzylidene Compounds / Q000737:chemistry*; D002855:Chromatography, Thin Layer; D006017:Glycolipids / Q000737:chemistry* / Q000302:isolation & purification; D008055:Lipids / Q000737:chemistry; D013058:Mass Spectrometry; D009161:Mycobacterium / Q000737:chemistry*; D009169:Mycobacterium tuberculosis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D001597:Benzylidene Compounds; D006017:Glycolipids; D008055:Lipids; C008901:phthiocerol dimycocerosate