1H NMR analysis of novel sialylated and fucosylated lactose-based oligosaccharides having linear GlcNAc(beta 1-6) Gal and Neu5Ac(alpha 2-6) GlcNAc sequences.
Three novel oligosaccharides of human infant faeces have been fully characterised by methylation analysis and 500/600 MHz 1H NMR spectroscopy including DQF-COSY, TQF-COSY, TOCSY and ROESY experiments. The oligosaccharides were shown to be lactose-based structures two of which were substituted at C-6 of Gal with either the Le(x) trisaccharide, Gal(beta 1-4)[Fuc(alpha 1-3)]GlcNAc(beta 1-, or Neu5Ac(alpha 2-6)Gal(beta 1-4)GlcNAc(beta 1-. They differ from other free oligosaccharides previously isolated from the human by having the (1-->6) linkage to Gal in the absence of a (1-->3) branch. The third oligosaccharide has Neu5Ac(alpha 2-6) linked to GlcNAc of the trisaccharide GlcNAc(beta 1-3)Gal(beta 1-4)Glc. This is a linear fragment of the disialylated tetrasaccharide sequence Neu5Ac(alpha 2-3)Gal(beta 1-3)[Neu5Ac(alpha 2-6)]GlcNAc(beta 1-found in the milk oligosaccharide disialyl LNT (the GlcNAc residue of the tetrasaccharide linked to lactose) and also of N-linked chains (GlcNAc linked to Man).
Bailey
D
D
Department of Biochemistry and Molecular Biology, University College London, UK.
Davies
M J
MJ
Routier
F H
FH
Bauer
C
C
Feeney
J
J
Hounsell
E F
EF
D001942:Breast Feeding; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D005243:Feces / Q000737:chemistry; D005643:Fucose / Q000378:metabolism*; D006801:Humans; D007223:Infant; D007785:Lactose / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D008969:Molecular Sequence Data; D015394:Molecular Structure; D019158:N-Acetylneuraminic Acid / Q000378:metabolism*; D009844:Oligosaccharides / Q000737:chemistry*
D009844:Oligosaccharides; D005643:Fucose; D019158:N-Acetylneuraminic Acid; D007785:Lactose