Thiolated hemicellulose as a versatile platform for one-pot click-type hydrogel synthesis
2015 (English)In: Biomacromolecules, ISSN 1525-7797, E-ISSN 1526-4602, Vol. 16, no 2, 667-674 p.Article in journal (Refereed) Published
A one-pot synthetic methodology for the thiolation of O-acetyl-galactoglucomannan (AcGGM) was developed to merge hemicellulose chemistry with "click" chemistry. This was realized by the AcGGM-mediated nucleophilic ring-opening of γ-thiobutyrolactone via the activation of the polysaccharide pendant hydroxyl groups. The incorporation of thiol functionalities onto the hemicellulose backbone was visualized by 1H and 13C NMR spectroscopy and was assessed by an Ellman's reagent assay of the thiol groups. The versatility of the thiolated AcGGM was elaborated and demonstrated by conducting several postmodification reactions together with hydrogel formation utilizing thiol-ene and thiol-Michael addition "click" reactions. The one-pot synthesis of thiolated AcGGM is a straightforward approach that can expand the applications of hemicelluloses derived from biomass by employing "click" chemistry.
Place, publisher, year, edition, pages
2015. Vol. 16, no 2, 667-674 p.
Addition reactions, Hydrogels, Nuclear magnetic resonance spectroscopy, Galactoglucomannan, Hydrogel formation, Hydroxyl groups, Michael additions, Nucleophilic ring opening, One-pot synthesis, Post-modification, Synthetic methodology
IdentifiersURN: urn:nbn:se:kth:diva-161070DOI: 10.1021/bm5018468ISI: 000349273000026ScopusID: 2-s2.0-84922511118OAI: oai:DiVA.org:kth-161070DiVA: diva2:793604
QC 201503092015-03-092015-03-092015-03-25Bibliographically approved