Synthesis of plant arabinogalactans

Abstract

Plant arabinogalactans consisting of a β-(1®6)-linked D-galactopyranosyl oligosaccharide backbone with α-(1®2)-L-arabinofuranosyl branches are synthesized based on the 1,2-anhydro galactopyranose technique, orthogonal (methoxydimethyl)methyl (MIP) and (2-naphthyl)methyl (NAP) protection strategy, and selective acylation or glycosylation method. The third method is the most simple and effective and it is also used for the synthesis of arabinogalactans composed of a β-(1®6)-linked D-galactopyranosyl oligosaccharide backbone with α-(1®3)-L-arabinofuranosyl branches.

Galactan synthesis in a single step via oligomerization of monosaccharides

“…As part of a project on the synthesis of glycan fragments derived from arabinogalactan proteins (AGPs) [17–18], we sought to prepare a β1→6 linked galactan as a chemical probe. We elected to prepare the galactan with a pyrene-containing aglycone to aid detection in subsequent biochemical studies.…”