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Issue 0, 1985
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Nitrosation of 2-amino-2-deoxy-D-galactitol; a model experiment for the study of reduced oligosaccharides derived from mucus glycoproteins

Abstract

Sequential nitrosation, and reduction with sodium cyanoborohydride, of 2-amino-2-deoxy-D-galactitol gave, as major products, 2-deoxy-D-lyxo-(and/or -xylo-)hexitol (39%) and glycerol (43%). Minor products included a hexitol and diastereoisomeric 2-deoxy-2-hydroxymethyl-D-pentitols (provisionally identified). Reduction of the nitrosation products with sodium borodeuteride gave 2-deoxy-D-hexitols with more deuterium at C-3 than at C-1. Glycerol was also shown to be a product of the nitrosation and reduction of 2-amino-2-deoxy-D-glucitol. The implications of these results for the nitrosation of the 2-amino-2-deoxy-D-galactitol-containing oligosaccharides derived from mucus glycoproteins are discussed.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1985, 2775-2777
Article type
Paper

Nitrosation of 2-amino-2-deoxy-D-galactitol; a model experiment for the study of reduced oligosaccharides derived from mucus glycoproteins

S. R. Carter, J. M. Williams and J. R. Clamp, J. Chem. Soc., Perkin Trans. 1, 1985, 2775
DOI: 10.1039/P19850002775

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