Analysis of the component aldehyde and alcohols in borohydride-reduced dialdehydes from hexosamine derivatives |
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Authors: | Susumu Honda Kazuaki Kakehi Kazunori Mukai |
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Institution: | Faculty of Pharmaceutical Sciences, Kinki University, Kowakae, Higashi-osakaJapan |
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Abstract: | Unlike the dialdehydes formed from neutral monosaccharide residues, the dialdehydes from hexosamine residues are resistant to acidified ethanethiol, leaving the hemiacetal bond intact. However, the borohydride-reduced dialdehydes are readily split into the component aldehyde and alcohols; gas Chromatographic analysis of their derivatives is useful for structural studies of hexosamine-containing carbohydrates. Investigation by these sequential derivatization reactions indicated that anomeric methyl 2-acetamido-2-deoxy--glucopyranosides were oxidized in normal Malapradian fashion, whereas 2-acetamido-2-deoxy--glucose was over-oxidized. The rate of oxidation of 2-acetamido-D-glucitol was very rapid; the oxidation product can also be analyzed by the direct dithioacetal method (mercaptalation followed by trimethylsilylation). |
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