title: A simple synthesis of octyl 3,6-di-O-(alpha-D-mannopyranosyl)-beta-D-mannopyranoside and its use as an acceptor for the assay of N-acetylglucosaminyltransferase-I activity.
abstract: A simple synthesis of octyl 3,6-di-O-(alpha-D-mannopyranosyl)-beta-D-mannopyranoside is described. The key features of the synthetic scheme are the formation of the beta-mannosidic linkage by 1-O-alkylation of 2,3,4,6-tetra-O-acetyl-alpha,beta-D-mannopyranose with octyl iodide and glycosylation of unprotected octyl beta-D-mannopyranoside using limiting acetobromomannose. The trisaccharide is shown to be an acceptor for N-acetylglucosaminyltransferase-I with KM of 585 microM.
authors.affiliation: Department of Chemistry, University of Alberta, Edmonton, Canada.
authors.forename: K J
authors.initials: KJ
authors.lastname: Kaur
authors.forename: O
authors.initials: O
authors.lastname: Hindsgaul
mesh_terms: D000478:Alkylation; D000818:Animals; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D005964:Glucosyltransferases / Q000378:metabolism*; D006031:Glycosylation; D008969:Molecular Sequence Data; D015394:Molecular Structure; D017351:N-Acetylglucosaminyltransferases; D011817:Rabbits; D014312:Trisaccharides / Q000138:chemical synthesis*
chemical_list: D014312:Trisaccharides; C076395:octyl 3,6-di-O-(mannopyranosyl)-mannopyranoside; D005964:Glucosyltransferases; D017351:N-Acetylglucosaminyltransferases; C024850:alpha-1,3-mannosyl-glycoprotein beta-1,2-N-acetylglucosaminyltransferase I