title: Modular modification of xylan with UV-initiated thiol-ene reaction.
abstract: Birch xylan was functionalized with various thiols through UV initiated radical thiol-ene reaction under mild conditions. Xylan was allylated through etherification with allyl glycidyl ether under alkaline conditions. The allylated xylan was then reacted with thiols containing varying functional groups: trimethylbenzyl mercaptan, dodecanethiol, thioglycolic acid, L-cysteine and cysteamine hydrochloride. The reactions were conducted under homogeneous conditions at room temperature, either in water (hydrophilic thiols) or in DMF (hydrophobic thiols). The effect of reaction parameters to the functionalization efficiency was studied, including, for example, thiol excess, thiol character, initiator amount and reaction mixture concentration. The reactions were fast and 100% conversion of allyl groups was reached in most cases, sometimes already within 10 min. Water as solvent resulted generally in faster reactions when compared to DMF, and it was possible to conduct the aqueous reaction even without added UV initiator. It was also possible to incorporate two functionalities simultaneously during one reaction into the xylan structure.
authors: VTT Technical Research Centre of Finland, Patruunantie 19, FI-05200 Rajamäki, Finland. Electronic address: leena.nurmi@vtt.fi.
authors: Leena
authors: L
authors: Nurmi
authors: VTT Technical Research Centre of Finland, Patruunantie 19, FI-05200 Rajamäki, Finland.
authors: Reeta
authors: R
authors: Salminen
authors: VTT Technical Research Centre of Finland, Biologinkuja 7, FI-02150 Espoo, Finland.
authors: Harri
authors: H
authors: Setälä
mesh_terms: D057930:Click Chemistry; D008958:Models, Molecular; D066244:Proton Magnetic Resonance Spectroscopy; D013438:Sulfhydryl Compounds / Q000737:chemistry / Q000528:radiation effects*; D014990:Xylans / Q000737:chemistry*
chemical_list: D013438:Sulfhydryl Compounds; D014990:Xylans
keywords: Chemical functionalization; Thiol-ene chemistry; Xylan