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Secondary plant cell walls are the repositories of renewable lignocellulosic biomass, which is composed of cellulose, hemicelluloses (HC) and lignins. Xylans are the major HC of cell walls of many plants, including grasses and broadleaved trees, representing up to 90% of the HC in cereals and 50% in soft wood[1]. Consequently xylans, which are composed of a main-chain built of D-xylosyl units that can be substituted by avariety of chemical moieties including acetyl groups, α-D-uronic acids and/or α-L-arabinose[1], represent a major source of pentoses in biorefineries. Therefore, the optimal valorization of these is vital for the sustainability of biorefinery processes. In this context, the development of new pentose-based products and the tools and processes to manufacture them is of considerable strategic value. Xylans can be hydrolyzed by endo-β-1,4-xylanases. These enzymes cleave the glycosidic bond linking two D-xylosyl units in presence of awater molecule acting as an acceptor. However, in the presence of acceptors other than water, certain xylanases display the ability to catalyze transglycosylation reactions, leading to the synthesis of xylose-based products[2], such as xylooligosaccharides or alkylpolypentosides, both of which are potentially valuable molecules that have commercial value. Nevertheless, the yields of enzyme-driven transglycosylation reactions are often low, due to primary competition with hydrolysis and secondary hydrolysis of the synthetic product.