New arylated chitosan derivatives by chemoenzymatic Michael addition to in situ generated quinones.

van den Broek, B. (Contributor), Boeriu, C. (Speaker)

Activity: Talk or presentationOral presentationProfessional


Oral presentation, abstract, conference paperChitosan, the N-deacetylated derivative of chitin, is a biocompatible, biodegradable and nontoxic natural material, with inherent antimicrobial properties owing to its specific structure and properties. Antibacterial, antifungal and insecticidal activity of chitosan has been demonstrated in numerous studies. However, the applicability of chitosan in aqueous solutions is limited by its cationic nature in acidic media and the lack of solubility in water or in organic solvents.
This paper reports the synthesis of novel hydroxyaryl-chitosan derivatives with increased solubility and pH-independent bioactive properties. Laccase, a multinuclear copper-containing oxidase, that is able to oxidise a wide range of phenolic compounds, was used to catalyze the oxidation of phenolic acids to the corresponding quinones, which were further reacting in situ with the nucleophilic amino group of the glucosamine building blocks of chitosan, via a Michael addition reaction.
Period3 Jul 20166 Jul 2016
Event typeConference
LocationWageningen, Netherlands
Degree of RecognitionInternational