A simple synthesis of octyl 3,6-di-O-(α-d-mannopyranosyl)-β-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-(α-d-mannopyranosyl)-β-d-mannopyranoside is described. The key features of the synthetic scheme are the formation of the β-mannosidic linkage by 1-O-alkylation of 2,3,4,6-tetra-O-acetyl-α,β-d-mannopyranose with octyl iodide and glycosylation of unprotected octyl β-d-mannopyranoside using limiting acetobromomannose. The trisaccharide is shown to be an acceptor for N-acetylglucosaminyltransferase-I with a KM of 585 μm. © 1991 Chapman and Hall Ltd.