End-group determination of oligosaccharides: a gas chromatography-mass spectrometry/mass spectrometry method for distinguishing between all D-aldohexoses and D-ketohexoses.
A method for end-group determination of oligosaccharides is described, which involves conversion of the reducing monosaccharide into a 1-deoxy-1-hydrazinohexitol heptaacetate (aldohexoses) or an epimeric pair of 2-deoxy-2-hydrazinohexitol heptaacetates (2-ketohexoses). Products are linear and unique to each aldohexose or ketohexose. Methods are reported for separation of all stereoisomers of the derivatives on single columns by gas chromatography. Gas chromatography-mass spectrometry/mass spectrometry with electron-impact ionization enabled the 1-deoxy-1-hydrazinohexitol heptaacetates and 2-deoxy-2-hydrazinohexitol heptaacetates to be independently identified in each others presence. Chemical-ionization mass spectrometry/mass spectrometry permitted derivatives to be identified in subpicomolar quantities. The non-acetylated compounds could also be identified as their hydrochlorides by 1H NMR spectroscopy.
Bendiak
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Department of Cellular and Structural Biology, University of Colorado Health Sciences Center, Denver 80262, USA. brad.bendiak@uchsc.edu
Fang
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D000447:Aldehydes / Q000737:chemistry; D002240:Carbohydrate Sequence; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods; D006601:Hexoses / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D009844:Oligosaccharides / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000447:Aldehydes; D006601:Hexoses; D007659:Ketones; D009844:Oligosaccharides