Structural analysis of nine oligosaccharides isolated from the urine of a blood group O, nonsecretor, woman during pregnancy and lactation.

Nine oligosaccharides have been isolated from urine collected from an O(H), Le(a+ b-), nonsecretor, woman during her pregnancy and subsequent lactation. One of them is a new hexasaccharide denoted lacto-N-neo-difucohexaose II: beta-D-Gal-(1 leads to 4)-[alpha-L-Fuc-(1 leads to 3)]-beta-D-GlcNAc-(1 leads to 3)-beta-D-Gal-(1 leads to 4)-[alpha-L-Fuc-(1 leads to 3)]-D-Glc. Seven of the remainder were identified as the milk oligosaccharides lacto-N-difucohexaose II, lacto-N-fucopentaose II and III, lacto-N-tetraose, 6'-galactosyllactose, 3-fucosyllactose, and lactose. The ninth component is a glucose-containing tetrasaccharide, alpha-D-Glc-(1 leads to 6)-alpha-D-Glc-(1 leads to 4)-alpha-D-Glc-(1 leads to 4)-D-Glc, previously found in normal human urine. The oligosaccharides were isolated by gel chromatography, preparative zone electrophoresis, and paper chromatography. The structures were determined by sugar and methylation analyses. Sequence analysis of tri- and tetra-saccharides was carried out by gas-liquid chromatography-mass spectrometry of reduced and permethylated oligosaccharide derivatives. The monosaccharide sequence in penta- and hexasaccharides was deduced from gas chromatographic-mass spectrometric studies of di- and trisaccharides obtained from partial acid hydrolysis of the parent compound. Anomeric configurations were deduced from the optical rotation.