Use of N-acetylglucosaminyltransferases I and II in the preparative synthesis of oligosaccharides.
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.
Kaur
K J
KJ
Department of Chemistry, University of Alberta, Edmonton, Canada.
Alton
G
G
Hindsgaul
O
O
D002240:Carbohydrate Sequence; D005964:Glucosyltransferases / Q000378:metabolism*; D008969:Molecular Sequence Data; D015394:Molecular Structure; D017351:N-Acetylglucosaminyltransferases; D009844:Oligosaccharides / Q000096:biosynthesis*
D009844:Oligosaccharides; D005964:Glucosyltransferases; D017351:N-Acetylglucosaminyltransferases; C024850:alpha-1,3-mannosyl-glycoprotein beta-1,2-N-acetylglucosaminyltransferase I; C063312:beta-1,3-galactosyl-0-glycosyl-glycoprotein beta-1,3-N-acetylglucosaminyltransferase