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.