Synthesis of Fungal Cell Wall Oligosaccharides and Their Ability to Trigger Plant Immune Responses

European J Org Chem. 2022 Jul 21;2022(27):e202200313. doi: 10.1002/ejoc.202200313. Epub 2022 Jul 15.


Oligosaccharide fragments of fungal cell wall glycans are important molecular probes for studying both the biology of fungi and fungal infections of humans, animals, and plants. The fungal cell wall contains large amounts of various polysaccharides that are ligands for pattern recognition receptors (PRRs), eliciting an immune response upon recognition. Towards the establishment of a glycan array platform for the identification of new ligands of plant PRRs, tri-, penta-, and heptasaccharide fragments of different cell wall polysaccharides were prepared. Chito- and β-(1→6)-gluco-oligosaccharides were synthesized by automated glycan assembly (AGA), and α-(1→3)- and α-(1→4)-gluco-oligosaccharides were synthesized in solution using a recently reported highly α-selective glycosylation methodology. Incubation of plants with the synthesized oligosaccharides revealed i) length dependence for plant activation by chito-oligosaccharides and ii) β-1,6-glucan oligosaccharides as a new class of glycans capable of triggering plant activation.

Keywords: Automated glycan assembly; Carbohydrate chemistry; Fungal cell wall; Pattern-triggered immunity; Plant immunity.