Oligosaccharides of human bronchial glycoproteins. Neutral di- and trisaccharides isolated from a patient suffering from chronic bronchitis.

Human bronchial glycoproteins from a patient suffering from chronic bronchitis were subjected to alkaline borohydride degradation and a heterogeneous mixture of reduced oligosaccharides and glycopeptides was obtained. The shortest neutral oligosaccharides were subsequently fractionated by DAX4 anion exchange chromatography into 12 fractions. Five major oligosaccharides were purified by preparative paper chromatography. Their structures were determined by using periodic oxidation, methylation analysis, gas liquid chromatography-mass spectrometry, and enzymatic degradation. Two oligosaccharides and three trisaccharides were characterized as galactose (Gal) beta 1 leads to 3 N-acetylgalactosaminitol (GalNActitol), N-acetylglucosamine (GlcNAc) beta 1 leads to 3 GalNActitol, Gal 1 leads to 4 GlcNAc 1 leads to 3 GalNActitol, GlcNAc 1 leads to 3 Gal 1 leads to 3 GalNActitol and fucose alpha 1 leads to 2 Gal beta 1 leads to 3 GalNActitol.