Thin-layer chromatography and mass spectrometry of pentafluorobenzylidene derivatives of members of the phthiocerol family from Mycobacterium tuberculosis and Mycobacterium marinum.
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.
Hartmann
S
S
Department of Chemistry, University of Newcastle, Newcastle upon Tyne, UK.
Mallet
A I
AI
Minnikin
D E
DE
Ridell
M
M
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
D000080:Acetals; D001597:Benzylidene Compounds; D006017:Glycolipids; D008055:Lipids; C008901:phthiocerol dimycocerosate