β-Xylopyranosides: synthesis and applications

Abstract

In recent years, β-xylopyranosides have attracted interest due to the development of biomass-derived molecules. This review focuses on general routes for the preparation of β-xylopyranosides by chemical and enzymatic pathways and their main uses.

Catalytic Upgrading of Biomass‐Derived Sugars with Acidic Nanoporous Materials: Structural Role in Carbon‐Chain Length Variation

“…Alkyl polyglycosides are carbohydrate‐based surfactants that have received much attention in chemical (e.g., cosmetic surfactants, food emulsifiers) and medical (e.g., antibacterial, antiviral agents) fields, owing to their good wettability, cleaning ability, and dermatological and ocular safety . As a typical example, alkyl glucosides are usually prepared and used as a nonionic surfactant.…”

Transglycosylation: A Key Reaction to Access Alkylpolyglycosides from Lignocellulosic Biomass

“…Because of miscibility issues, industrial processing of carbohydrate syrupsi nvolves ap reliminary glycosylation with as hort-chain alkyl alcohol followed by their transglycosylation with af atty alcohol. [11] In contrast to conventional catalytic routes, this method allows the production of pure anomeric glycosides (b form) through enzymatically catalyzed glycosylation or transglycosylation of either protected monomeric sugars or pretreated and isolated polysaccharides. [10] During the glycosylationr eaction, monomeric carbohydrates tend to polymerize affording alkylpolyglycosides, rather than alkylmonoglycosides, with a typical degree of polymerization of about 1.1-2.2, depending on the starting carbohydrate source.…”

‘Click’‐xylosides as initiators of the biosynthesis of glycosaminoglycans: Comparison of mono‐xylosides with xylobiosides

“…Xyloside derivatives can be obtained either by classical chemical strategies (Fischer glycosylation, Koenigs–Knorr reaction…) or by enzymatic reactions using glycosidases . We recently developed a two‐step chemo‐enzymatic synthesis of a series of xylosides and xylobiosides from xylans as raw material .…”

“…The main effects observed were the growth inhibition of tumor cells, [20,[22][23][24][25][26][27] the activation of fibroblast growth factors, [28] and antithrombotic effects. [29] Xyloside derivatives can be obtained either by classical chemical strategies (Fischer glycosylation, Koenigs-Knorr reaction…) [30,31] or by enzymatic reactions using glycosidases. [31,32] We recently developed a two-step chemoenzymatic synthesis of a series of xylosides and xylobiosides from xylans as raw material.…”

“…[29] Xyloside derivatives can be obtained either by classical chemical strategies (Fischer glycosylation, Koenigs-Knorr reaction…) [30,31] or by enzymatic reactions using glycosidases. [31,32] We recently developed a two-step chemoenzymatic synthesis of a series of xylosides and xylobiosides from xylans as raw material. [33] In a first step, an enzymatic synthesis of propargyl xyloside 1 and propargyl xylobioside 2 was carried out from beechwood xylans and propargyl alcohol using a commercially available xylanase.…”