Novel Hybrid Morpholino-Glycopeptides with the Amino Acid Nitrogen Replacing C-3 of the Pyranose Ring

Article abstract of DOI:10.1055/s-1997-800

Periodate oxidation of glycopyranosides yields dialdehydes that can be reductively aminated in the presence of amino acids to produce hybrid glycopeptides where the amino acid nitrogen is inserted into the resulting 2,4-dideoxypyranoside at position 3. Nine such 3-morpholino derivatives were prepared, including a disaccharide analog of N-acetyllactosamine (βGal(1→4)βGlcNAc) where the nitrogen of glycine was inserted into the galactose ring. The resulting hybrid disaccharide was an excellent substrate for a milk fucosyltransferase which converted it to a novel functionalized LeX mimic.