Use of N-acetylglucosaminyltransferases I and II in the preparative synthesis of oligosaccharides.

Article abstract of DOI:10.1016/0008-6215(91)80118-7

8-Methoxycarbonyloctyl 3,5-di-O-(alpha-D-mannopyranosyl)-beta-D-mannopyranoside (1) has been synthesised chemically. Compound 1 is a substrate for N-acetylglucosaminyltransferase-I (GlcNAcT-I), which transfers a beta-D-GlcpNAc residue from UDP-GlcpNAc to position 2 of the alpha-Man-(1----3) unit to produce 2. In turn, the tetrasaccharide 2 is an acceptor for GlcNAcT-II which, in the presence of UDP-GlcpNAc, converts 2 into 8-methoxycarbonyloctyl 3,6-di-O-[2-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-alpha-D- mannopyranosyl]-beta-D-mannopyranoside (3). These conversions were carried out on a 50-100 mg scale using enzyme preparations obtained from rabbit liver in a single step by affinity chromatography.