Synthesis of a N-glycan nonasaccharide of the bisecting type with additional core-fucose

A chemical synthesis was developed for N-glycans substituted with core-fucose and an additional bisecting GlcNAc (LEC10 motif). The synthesis was conducted using a suitably functionalized N-glycan pentasaccharide assembled from modular building blocks. Selective introduction of the bisecting GlcNAc residue was followed by attachment of the alpha 1,6-arm and core-fucose. After introduction of an ammohexanoyl spacer the nonasaccharide was completely deprotected providing a substrate for enzymatic elongation and conjugation to proteins for further biological studies. (c) 2005 Elsevier Ltd. All rights reserved.