Determination of the absolute configuration of sugar residues using gas chromatography. Method with potential for elimination of references.
The absolute configuration of a sugar can be determined by gas-liquid chromatography of the acetylated or trimethylsilylated dithioacetals from 1-phenylethanethiol. The isolation of both enantiomers of 1-phenylethanethiol is also described. Using the acetates and both thiol reagents the absolute configuration of C-2 can be determined, provided it is a hydroxyl group, with great certainty. A new way of determining the absolute configuration of sugars, without references, is thereby provided. The sugars analysed include aldoses, deoxyaldoses, 2-acetamido-2-deoxyaldoses and uronic acids. The analysis is made using columns with non-chiral stationary phase and the electron impact mass spectra of the acetylated and trimethylsilylated bis(1-phenylethyl)dithioacetals are described.
Lindqvist
L
L
Department of Immunology, Microbiology, Pathology and Infectious Diseases, Karolinska Institutet, Huddinge Hospital, Sweden.
Jansson
P E
PE
D000080:Acetals / Q000737:chemistry; D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000737:chemistry* / Q000302:isolation & purification; D002849:Chromatography, Gas; D007700:Kinetics; D013058:Mass Spectrometry; D008968:Molecular Conformation; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry / Q000302:isolation & purification; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification*; D014297:Trimethylsilyl Compounds / Q000737:chemistry
D000080:Acetals; D002241:Carbohydrates; D009005:Monosaccharides; D013438:Sulfhydryl Compounds; D014297:Trimethylsilyl Compounds; C106744:1-phenylethanethiol