Solid‐Phase Synthesis of Clickable Psicofuranose Glycocarbamates and Application of Their Self‐Assembled Nanovesicles for Curcumin Encapsulation

Abstract

Among the cyclic forms of carbohydrates, pyranoside derivatives have widely contributed to the well‐defined nanoassemblies. However, nanoassemblies originating from furanoside derivatives/oligomers, excluding nucleosides are underrepresented. Herein, we discuss the design and solid‐phase synthesis of homoligomers of a new class of clickable psicofuranose glycocarbamates that display nanovesicular/spherical nanostructures, an occurrence rarely observed in furanoside oligomers. The key intermediate, D‐(‐)‐fructose derived 2‐azido psicofuranose carbonate, was converted into dimeric and tetrameric azido‐glycocarbamates on solid‐phase which on subsequent “Click” reaction provided triazolyl glycocarbamates. These amphiphilic glycocarbamates self‐assembled into thermally and proteolytically stable spherical vesicles of 200‐800 nm size with visible hollow nature in CH3OH and tightly packed sphericals in CH3OH‐H2O. These nanostructures are characterized by various microscopy techniques. Effect of Cu+2 and Zn+2 ions, various cationic stimuli on the morphology of these nanostructures was studied. Hydrophobic drug curcumin was encapsulated in the hollow vesicles and release of the drug was investigated.