Poly(methyl 6-acryloyl-β-d-glucosaminoside) as a Cationic Glycomimetic of Chitosan

Biomacromolecules
Walter T Liau, Andrea M Kasko

Abstract

Chitosan, a cationic polysaccharide derived from one of the most abundant natural polymers, chitin, has been investigated extensively for its antimicrobial properties. However, it suffers from the inherent drawbacks of natural products such as batch-to-batch variability, limited supply, contamination, and potential adverse reaction. Additionally, its solubility depends on the degree of deacetylation and pH, as it is only soluble under acidic conditions. As an alternative to chitosan, we synthesized the protected cationic glycomimetic monomer methyl N-Fmoc-6-acryloyl-β-d-glucosaminoside from glucosamine. This monomer retains structural features critical to recapitulating the properties of the chitosan repeat unit, namely, the pKa of the protonated amine. We optimized the free radical polymerization of methyl N-Fmoc-6-acryloyl-β-d-glucosaminoside and fractionated the resultant poly(methyl N-Fmoc-6-acryloyl-β-d-glucosaminoside) to obtain a range of molecular weights. Following Fmoc deprotection, the cationic glycopolymers retained 95% of their expected amine content by mass and exhibited a pKa of 6.61. Poly(methyl 6-acryloyl-β-d-glucosaminoside) mimicked the molecular weight-dependent bacterial inhibitory property of chitosan in a...Continue Reading

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Citations

Oct 23, 2019·Acta Pharmaceutica : a Quarterly Journal of Croatian Pharmaceutical Society and Slovenian Pharmaceutical Society, Dealing with All Branches of Pharmacy and Allied Sciences·Bisera Jurišić DukovskiJasmina Lovrić
Nov 25, 2020·The Journal of Organic Chemistry·Yuan XuXue-Wei Liu

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