title: Novel thiol- amine- and amino acid functional xylan derivatives synthesized by thiol-ene reaction.
abstract: In the present work, novel thioether xylans were synthesized via a simple procedure using water as solvent. First, allyl groups were introduced on the backbone of xylan by etherification of allyl chloride in aqueous alkaline conditions at 40°C, providing degree of substitution (DS) values up to 0.49. On the second step, the allyl groups were reacted with thioacetic acid, cysteamine hydrochloride or cysteine providing novel thiol-, amine- or amino acid functionalized xylans. The presented modular approach offers broad possibilities for developing new polysaccharide based materials. The thioacetic acid - ene reaction is reported for the first time for polysaccharide modification, yielding a protected thiol that can be stored at atmospheric conditions and can be deprotected by simple hydrolysis just prior to use, providing a versatile water soluble polythiol. The free thiol-groups were utilized for hydrogel formation through thiol-thiol oxidative coupling, allowing good control over the hydrogel shape, such as 3D hydrogel scaffolds and cross-linked foams. Further, the thiol-containing xylan was used to modify filter paper surface by a simple dipping method, which provides a novel and convenient way for introducing thiol-functionality on paper surface.
authors.affiliation: Department of Biotechnology and Chemical Technology, Aalto University School of Chemical Technology, Kemistintie 1, 02150 Espoo, Finland.
authors.forename: Nikolaos
authors.initials: N
authors.lastname: Pahimanolis
authors.affiliation: Finnish Natural Resources Institute (Luke) , Jokiniemenkuja 1, P.O.Box 18, 01301 Vantaa, Finland.
authors.forename: Petri
authors.initials: P
authors.lastname: Kilpeläinen
authors.affiliation: Department of Chemical Engineering and Applied Chemistry, University of Toronto, 200 College Street, Toronto, ON, M5S 3E5, Canada.
authors.forename: Emma
authors.initials: E
authors.lastname: Master
authors.affiliation: Finnish Natural Resources Institute (Luke) , Jokiniemenkuja 1, P.O.Box 18, 01301 Vantaa, Finland.
authors.forename: Hannu
authors.initials: H
authors.lastname: Ilvesniemi
authors.affiliation: Department of Biotechnology and Chemical Technology, Aalto University School of Chemical Technology, Kemistintie 1, 02150 Espoo, Finland. Electronic address: jukka.seppala@aalto.fi.
authors.forename: Jukka
authors.initials: J
authors.lastname: Seppälä
mesh_terms: D000588:Amines / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D057930:Click Chemistry / Q000379:methods*; D003432:Cross-Linking Reagents / Q000737:chemistry; D020136:Hydrogel, Polyethylene Glycol Dimethacrylate / Q000737:chemistry; D066244:Proton Magnetic Resonance Spectroscopy; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D014990:Xylans / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000588:Amines; D000596:Amino Acids; D003432:Cross-Linking Reagents; D013438:Sulfhydryl Compounds; D014990:Xylans; D020136:Hydrogel, Polyethylene Glycol Dimethacrylate
keywords: Click chemistry; Hydrogel; Modification of polysaccharides; Polythiol; Thiol-ene; Thiomer; Xylan