Combined chemical-enzymic synthesis of a dideoxypentasaccharide for use in a study of the specificity of N-acetyl-glucosaminyltransferase-III.
The biantennary oligosaccharide glycoside beta-D-GlcpNAc-(1----2)-alpha-D- Manp-(1----3)- [beta-D-GlcpNAc-(1----2)-alpha-D-Manp-(1----6)]-beta-D-Manp- OR is a potential substrate for N-acetylglucosaminyltransferases (GlcNAcTs) III-V. The dideoxypentasaccharide glycoside beta-D-GlcpNAc-(1----2)-4- deoxy-alpha-D-lyxo-Hexp-(1----3)- [beta-DGlcpNAc-(1----2)-6-deoxy-alpha-D-Manp-(1----6)] beta-D-Manp-O(CH2)7CH3 (5), where the hydroxyl groups that would be acted on by GlcNAcTs IV and V have been removed, was prepared as a possible specific acceptor for GlcNAcT-III. The strategy involved the chemical synthesis of beta-D-GlcpNAc-(1----2)-4-deoxy-alpha-D-lyxo-Hexp-(1----3)-] 6- deoxy-alpha-D-Manp-(1----6)]-beta-D-Manp-O)CH2)7CH3 and then addition of the last GlcpNAc residue using partially purified GlcNAcT-II from rabbit liver. Preliminary results, using detergent extracts from rat kidney, indicate that 5 is an acceptor for a GlcNAcT whose identity remains to be established.
Kaur
K J
KJ
Department of Chemistry, University of Alberta, Edmonton, Canada.
Hindsgaul
O
O
D000818:Animals; D002240:Carbohydrate Sequence; D005964:Glucosyltransferases / Q000378:metabolism*; D007668:Kidney / Q000201:enzymology; D008969:Molecular Sequence Data; D017351:N-Acetylglucosaminyltransferases; D009844:Oligosaccharides / Q000737:chemistry* / Q000378:metabolism; D051381:Rats; D012210:Rhamnose / Q000031:analogs & derivatives*; D013379:Substrate Specificity
D009844:Oligosaccharides; D005964:Glucosyltransferases; D017351:N-Acetylglucosaminyltransferases; C037649:N-acetyllactosaminide beta-1,6-N-acetylglucosaminyltransferase; D012210:Rhamnose