title: Structural determination of novel lacto-N-decaose and its monofucosylated analogue from human milk by electrospray tandem mass spectrometry and 1H NMR spectroscopy.
abstract: We have isolated and characterised two neutral oligosaccharides, one nonfucosylated and the other monofucosylated, from human milk that are based on the doubly branched lacto-N-decaose core. Their structures have been determined by a combined use of electrospray tandem mass spectrometry (ES-MS/MS) and NMR spectroscopy. The sequences of the three branches resulted from the double-branching, including the identity and location of the blood-group-related Lewis determinant and partial linkages, were elucidated by the unique method of high sensitivity negative-ion ES-MS/MS analysis. Their full structure assignment was completed by methylation analysis and 1H NMR. The monofucosylated lacto-N-decaose, Galbeta1-4(Fucalpha1-3)GlcNAcbeta1-6(Galbeta1-3GlcNAcbeta1-3)Galbeta1-4GlcNAcbeta1-6(Galbeta1-3GlcNAcbeta1-3)Galbeta1-4Glc is a novel sequence, whereas the nonfucosylated lacto-N-decaose, Galbeta1-4GlcNAcbeta1-6(Galbeta1-3GlcNAcbeta1-3)Galbeta1-4GlcNAcbeta1-6(Galbeta1-3GlcNAcbeta1-3)Galbeta1-4Glc, has not been isolated and identified as an individual oligosaccharide.
authors.affiliation: MRC Glycosciences Laboratory, Imperial College Faculty of Medicine, Northwick Park and St. Mark's Campus, Watford Road, Harrow, Middlesex HA1 3UJ, United Kingdom. w.chai@imperial.ac.uk
authors.forename: Wengang
authors.initials: W
authors.lastname: Chai
authors.forename: Vladimir E
authors.initials: VE
authors.lastname: Piskarev
authors.forename: Yibing
authors.initials: Y
authors.lastname: Zhang
authors.forename: Alexander M
authors.initials: AM
authors.lastname: Lawson
authors.forename: Heide
authors.initials: H
authors.lastname: Kogelberg
mesh_terms: D001789:Blood Group Antigens / Q000737:chemistry; D002240:Carbohydrate Sequence; D005260:Female; D006801:Humans; D008745:Methylation; D008895:Milk, Human / Q000737:chemistry*; D008969:Molecular Sequence Data; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009844:Oligosaccharides / Q000737:chemistry* / Q000302:isolation & purification; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D001789:Blood Group Antigens; D009844:Oligosaccharides