Synthese von modifizierten Oligosacchariden der N-Glycoproteine als Substrate für N-Acetylglucosaminyltransferase I

Abstract

In the synthesis of modified derivatives of octyl O-(α- d-mannopyranosyl)-(1 → 3)- O-[(α- d-mannopyrasonyl)-(1 → 6)-β- d-mannopyranoside, a 4,5-epoxypentyl, a 4-diazirinopentyl, and a 5-(iodoacetamido)pentyl group were attached to the 3″-OH of the trisaccharide. The diazirino derivative may be especially suitable for photolabeling of the active site of N-acetylglucosaminyltransferase I (GlcNAcT-I). In addition, the 2′-OH group of the above-mentioned trisaccharide was reduced to a 2′-deoxy group and substituted 2′- O-methyl group.