Structure of sialyloligosaccharides isolated from bonnet monkey (Macaca radiata) cervical mucus glycoproteins exhibiting multiple blood group activities

Abstract

Mucin glycoproteins purified from cervical epithelial secretion of the bonnet monkey (Macaca radiata) exhibit multiple blood group activities. Alkaline borohydride reductive cleavage resulted in a mixture of neutral and acidic oligosaccharide-alditols. By high-performance liquid chromatography, seven oligosaccharides (A-4-1 to A-4-7) have been purified from the monosialyloligosaccharide fraction (A-4). Based on the results of 500-MHz 1H NMR spectroscopy, in conjunction with sugar analysis and immunological assays, we propose the following structures for these oligosaccharides. (formula: see text) These structures imply that either the A, B, or H determinant may be found in combination with the Cad/Sda determinant; the oligosaccharides identified, together, account for the blood group activities exhibited by the cervical mucus.