Patent ID: 7943763
Filing Date: 2011-05-17
Classification: C07K,C08B,Y02P

Abstract:
1. A process for preparing a glycopeptide having at least one asparagine-linked oligosaccharide at a desired position of the peptide chain thereof, the process comprising: (1) esterifying a hydroxyl group of a resin having the hydroxyl group and a carboxyl group of an amino acid having amino group nitrogen protected with a fat-soluble protective group, (2) removing the fat-soluble protective group to form a free amino group, (3) amidating the free amino group and a carboxyl group of an amino acid having amino group nitrogen protected with a fat-soluble protective group, (4) removing the fat-soluble protective group to form a free amino group, (5) repeating the steps (3) and (4) at least once, (6) preparing an asparagine-linked disialooligosaccharide or an asparagine-linked monosialooligosaccharide having amino group nitrogen protected with a fat-soluble protective group and the carboxyl group of the sialic acid protected with a benzyl or allyl group, wherein the benzyl or allyl group is introduced into the carboxyl group of the sialic acid under a condition of pH 5 to 6, (7) amidating the free amino group and a carboxyl group of the asparagine portion of the asparagine-linked disialooligosaccharide or the asparagine-linked monosialooligosaccharide having amino group nitrogen protected with a fat-soluble protective group and the carboxyl group of the sialic acid protected with a benzyl or allyl group, (8) removing the fat-soluble protective group to form a free amino group, (9) amidating the free amino group and a carboxyl group of an amino acid having amino group nitrogen protected with a fat-soluble protective group, (10) repeating the steps (8) and (9) at least once, (11) removing the fat-soluble protective group to form a free amino group, and cutting off the resin with an acid.