A simple synthesis of octyl 3,6-di-O-(?-d-mannopyranosyl)-?-d-mannopyranoside and its use as an acceptor for the assay ofN-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.