Chemical synthesis of β-arabinofuranosyl containing oligosaccharides derived from plant cell wall extensins

Abstract

Extensins are plant-derived glycoproteins that are densely modified by oligo-arabinofuranosides linked to hydroxyproline residues. These glycoproteins have been implicated in many aspects of plant growth and development. Here, we describe the chemical synthesis of a tetrameric β(1–2)-linked arabinofuranoside that is capped by an α(1–3)-arabinofuranoside and a similar trisaccharide lacking the capping moiety. The challenging β(1–2)-linked arabinofuranosides were installed by using an arabinofuranosyl donor protected with 3,5-O-(di-tert-butylsilane) and a C-2 2-methylnaphthyl (Nap) ether. It was found that the cyclic silane-protecting group of the glycosyl donor greatly increased β-anomeric selectivity. It was, however, imperative to remove the silane-protecting group of an arabinosyl acceptor to achieve optimal anomeric selectivities. The anomeric linker of the synthetic compounds was modified by a biotin moiety for immobilization of the compounds to microtiter plates coated with streptavidine. The resulting microtiter plates were employed to screen for binding against a panel of antibodies elicited against plant cell wall polysaccharides.