Isolation and Structural Studies of Human Milk Oligosaccharides That Are Reactive with a Monoclonal Antibody MSW 1131

Abstract

We have determined the structures of six oligosaccharides isolated from human milk using a monoclonal antibody, MSW 113. The isolation involved affinity chromatography on a column of the immobilized monoclonal antibody and high-performance liquid chromatography. From the results of 500 and 600 mHz 1H NMR spectroscopy and fast atom bombardment-mass spectrometry their structures were deduced to be: [formula; see text] Two of these oligosaccharides, numbers 4 and 5, have not previously been described. All of them bound to MSW 113, but their reactivities are weaker than those of sialyl-Le(a) oligosaccharides. The results indicate that MSW 113 reacts with oligosaccharides with the mono- and disialyl-Le(a), and other sialyl type 1 structures.

Chemical Diversity in the Sialic Acids and Related α-Keto Acids: An Evolutionary Perspective

“…In most cases they occupy the distal (outermost) end of glycan chains, being commonly linked via an α2−3 linkage to Gal, via an α2−6 linkage to Gal and GalNAc, or via an α2−8 linkage to another sialic acid . Such linkages as α2−3 linkage to GalNAc, , α2−6 linkage to GlcNAc , and Glc, α2−4 linkage to Gal and GlcNAc, α2−9 linkage to another sialic acid, and a Neu5Gc oligomer linked via hydroxyl group of N- glycolyl also exist but are rare (some are only found, so far, in echinoderms). There are also some examples in echinoderms and amphibians where the sialic acids are found as internal residues, i.e., substituted at one or more hydroxyl groups by another sugar other than sialic acid. , These “outer” sugars may be considered as additional sialic acid “modifications”.…”

The trail of my studies on glycoproteins from enterokinase to tumor markers

“…41) By fractionating oligosaccharides in the eluate on a column of TSK-GEL NH 2 , 14 oligosaccharides could be isolated. 42) …”

“…42) A was sialyl-lacto-N-tetraose (CA 50), which is known as antigen recognized by the C-50 antibody, 42) and is a useful tumor marker for pancreatic cancer. B was an antigen for the FH 9 antibody and is frequently detected in liver and pancreatic cancer.…”

“…49) It should be noted that none of oligosaccharides A–D had the sialyl-Le a structure, yet they reacted with MSW 113. 42) …”