Occurrence of tetra- and pentasaccharides with the sialyl-Le(a) structure in human milk.
The occurrence of two novel oligosaccharides in human milk was investigated. These oligosaccharides were purified by affinity chromatography on a column of an immobilized monoclonal antibody, MSW 113. Structural studies, involving 500-MHz 1H NMR spectroscopy and fast atom bombardment-mass spectrometry, indicated the structures of these compounds to be NeuAc alpha 2----3Gal beta 1----3(Fuc alpha 1----4) GlcNAc and NeuAc alpha 2----3Gal beta 1----3(Fuc alpha 1----4) GlcNac beta 1----3Gal. This constitutes the first evidence for the occurrence of N-acetylglucosamine or galactose as the reducing-end residue of human milk oligosaccharides. These two oligosaccharides bound MSW 113 to nearly the same extent as sialyl-Lea hexasaccharide but to another sialyl-Le(a) structure-directed monoclonal antibody, NS-19-9, only weakly.
Kitagawa
H
H
Department of Biological Chemistry, Faculty of Pharmaceutical Sciences, Kyoto University, Japan.
Nakada
H
H
Numata
Y
Y
Kurosaka
A
A
Fukui
S
S
Funakoshi
I
I
Kawasaki
T
T
Shimada
I
I
Inagaki
F
F
Yamashina
I
I
D015295:Antigens, Tumor-Associated, Carbohydrate; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D005260:Female; D006801:Humans; D013058:Mass Spectrometry; D008895:Milk, Human / Q000032:analysis*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000032:analysis; D012689:Sequence Homology, Nucleic Acid
D015295:Antigens, Tumor-Associated, Carbohydrate; D009844:Oligosaccharides; C058981:sialyl-Le(a) oligosaccharide