Primary structure of four human milk octa-, nona-, and undeca-saccharides established by 1H and 13C-nuclear magnetic resonance spectroscopy
1992
The structures of two octasaccharides, one nonasaccharide, and one undecasaccharide, isolated from human milk, have been investigated by 1H- and 13C-nuclear magnetic resonance spectroscopy. The structures of these oligosaccharides are: beta-D-Galp-(1 leads to 4)-[alpha-L-Fucp-(1 leads to 3)]-beta-D-GlcpNAc-(1 leads to 3)-beta-D-Galp-(1 leads to 4)-[alpha-L-Fucp-(1 leads to 3)]-beta-D-GlcpNAc-(1 leads to 3)-beta-D-Galp-(1 leads to 4)-D-Glc; beta-D-GALp-(1 leads to 3)-[alpha-L-Fucp-(1 leads to 4)]-beta-D-GlcpNAc-(1 leads to 3) -beta-D-Galp-(1 leads to 4)-[alpha-L-Fucp-(1 leads to 3)]-beta-D-Glcp Nac-(1 leads to 3)-beta-D-Galp-(1 leads to 4)-D-Glc; beta-D-Galp-(1 leads to 4)-[alpha-L-Fucp-(1 leads to 3)]-beta-D-Glcp NAc-(1 leads to 6)-[alpha-L-Fucp-(1 leads to 2)-beta-D-Gal-(1 leads to 3)-[alpha-L-Fucp-(1 leads to 4)]-beta-D-GlcpNAc-(1 leads to 3)]-beta-D-Galp-(1 leads to 4)-D-Glc; and alpha-L-Fucp-(1 leads to 2)-beta-D-Galp-(1 leads to 3)-beta-D-Glcp Nac-(1 leads to 3)-beta-D-Galp-(1 leads to 4)-[alpha-L-Fucp-(1 leads to 3-beta-D-Glcp NAc-(1 leads to 6)-[alpha-L-Fucp-(1 leads to 2)-beta-D-Galp-(1 leads to 3)-beta-D-Glcp Nac-(1 leads to 3)]-beta-D-Galp-(1 leads to 4)-D-Glc. The two octasaccharides have been previously isolated from human milk as a mixture, and in a pure form from new-born feces, but the n.m.r. data were not provided. These two octasaccharides display the di-Lewis X and the composite Lewis A Lewis X antigenic determinant, previously described as neo-antigens of adenocarcinoma cell lines.
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