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The rapid emergence of multidrug-resistant (MDR) bacteria represents a critical global health threat, underscoring the urgent need for alternative antimicrobial strategies beyond conventional antibiotics. In this study, we report the synthesis of novel biobased antimicrobial polymers bearing quaternary ammonium salts, derived from sustainable feedstocks, maleic anhydride, dimethylaminobenzaldehyde, and furfurylamine. The functional tricyclic oxanorbornene lactam monomer is polymerized via ring opening metathesis polymerization, yielding well-defined polymers with controlled molar masses and low dispersity. Structural characterization is performed using 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, and the polymerization kinetics is monitored by online H NMR spectroscopy. The quaternized biobased polymers demonstrate potent broad-spectrum antimicrobial activity against three clinically isolated MDR bacterial strains. They exhibit minimum inhibitory concentrations (MICs) that are significantly lower than those of several conventional antibiotics while also showing low hemolytic activity toward mammalian cells. This study highlights the potential of bioderived ROMP polymers as promising, sustainable antimicrobial polymers for combating the growing threat of antimicrobial resistance.
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http://dx.doi.org/10.1021/acsabm.4c01924 | DOI Listing |
Macromolecules
April 2025
Utrecht University, Organic Chemistry & Catalysis, Institute for Sustainable and Circular Chemistry, Faculty of Science, Utrecht 3584 CG, the Netherlands.
Bioderived monomers, readily available from biomass via atom- and redox-efficient processes, will need to play a major role in the development of sustainable polymeric materials. Here, we show that a family of tricyclic monomers, efficiently made from biobased furans via Diels-Alder chemistry, allows the production of polyenes with diverse thermo/physical properties through ring opening metathesis polymerization (ROMP). Via small structural variations, we offer insight into the intricacies of monomer design and its implications for polymerization.
View Article and Find Full Text PDFACS Appl Bio Mater
February 2025
Leibniz-Institut für Polymerforschung Dresden e.V., Hohe Straße 6, 01069 Dresden, Germany.
The rapid emergence of multidrug-resistant (MDR) bacteria represents a critical global health threat, underscoring the urgent need for alternative antimicrobial strategies beyond conventional antibiotics. In this study, we report the synthesis of novel biobased antimicrobial polymers bearing quaternary ammonium salts, derived from sustainable feedstocks, maleic anhydride, dimethylaminobenzaldehyde, and furfurylamine. The functional tricyclic oxanorbornene lactam monomer is polymerized via ring opening metathesis polymerization, yielding well-defined polymers with controlled molar masses and low dispersity.
View Article and Find Full Text PDFJ Am Chem Soc
December 2024
Organic Chemistry and Catalysis, Institute for Sustainable and Circular Chemistry, Faculty of Science, Utrecht University, Universiteitsweg 99, 3584 CG Utrecht, The Netherlands.
New polymers, properly designed for end-of-life and efficiently formed from renewable carbon, are key to the transition to a more sustainable circular plastics economy. Ring-opening polymerization (ROP) of bicyclic lactones is a promising method for the production of intrinsically recyclable polyesters, but most lactone monomers lack an efficient synthesis route from biobased starting materials, even though this is essential to sustainably account for material loss during the life cycle. Herein, we present the exceptionally rapid and controlled polymerization of a fully biobased tricyclic oxanorbornene-fused γ-butyrolactone monomer ().
View Article and Find Full Text PDFMacromol Rapid Commun
April 2018
School of Biology, Chemistry and Forensic Science, Faculty of Science and Engineering, University of Wolverhampton, Wulfruna Street, Wolverhampton, WV1 1LY, UK.
The synthesis of a range of alkyl esters (methyl, n-butyl, and n-decyl) prepared via Steglich esterification of the thermodynamically controlled exo, exo Diels-Alder adduct of furfuryl alcohol and maleic anhydride is reported. Subsequent ring-opening metathesis polymerization of these bio-derivable tricyclic oxanorbornene analogs delivers polymers with targeted molar mass and low molar mass dispersity. The polymerizations are rapid with complete monomer conversion achieved within 15 min.
View Article and Find Full Text PDFOrg Biomol Chem
August 2010
Research group SynBioC, Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, B-9000, Ghent, Belgium.
Phosphonylated azaheterocycles are an important class of compounds with high biological potential as conformationally restricted bioisosteres of amino acids. Therefore, it is of interest to synthesize conformationally constrained amino phosphonates. We wanted to investigate possible routes via ring opening of alpha-amino phosphonates with an oxanorbornene skeleton, as these can be synthesized with high stereoselectivity.
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