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Novel heterocyclic chitosan derivatives and their derived nanoparticles: Catalytic and antibacterial properties
International Journal of Biological Macromolecules ( IF 8.2 ) Pub Date : 2020-01-25 , DOI: 10.1016/j.ijbiomac.2019.12.277
Andreii S. Kritchenkov , Anton R. Egorov , Alexey A. Artemjev , Ilya S. Kritchenkov , Olga V. Volkova , Elena I. Kiprushkina , Ludmila A. Zabodalova , Elena P. Suchkova , Niyaz Z. Yagafarov , Alexander G. Tskhovrebov , Aleh V. Kurliuk , Tatsiana V. Shakola , Victor N. Khrustalev

The metal-assisted nitrone-nitrile cycloaddition reaction is apply to empower chitosan chemistry. The ultrasonic irradiation has proven to efficiently accelerate the cycloaddition affording new heterocyclic (1,2,4-oxadiazoline) chitosan derivatives and avoiding ultrasonic degradation of the chitosan macromolecules. By varying the nitrone nature, both water- and toluene-soluble chitosan derivatives were successfully synthesized. Relying on the ionic gelation approach nanoparticles of heterocyclic chitosan derivatives were prepared. Water-soluble chitosan derivative demonstrated a high antibacterial activity coupled with low toxicity. The toxicity of the synthesized heterocyclic chitosan derivatives and their based nanoparticles are comparable with those of the starting chitosan, while their antibacterial activity is superior. Toluene-soluble derivatives are shown to be efficient homogeneous catalysts towards monoglyceride synthesis via the epoxide ring opening. They efficiently catalyze selective conversion of fatty acids and glycidol into corresponding monoglycerides allowing one to simplify significantly the procedure for separating the reaction product from the catalyst for its recovery and reusage.



中文翻译:

新型杂环壳聚糖衍生物及其衍生的纳米颗粒:催化和抗菌性能

金属辅助的腈-腈环加成反应适用于增强壳聚糖的化学作用。已经证明,超声辐射可以有效地加速环加成反应,从而提供新的杂环(1,2,4-恶二唑啉)壳聚糖衍生物,并避免了壳聚糖大分子的超声降解。通过改变硝酮的性质,成功合成了水溶性和甲苯可溶性壳聚糖衍生物。依靠离子凝胶法,制备了杂环壳聚糖衍生物的纳米粒子。水溶性壳聚糖衍生物显示出高抗菌活性和低毒性。合成的杂环壳聚糖衍生物及其基纳米粒子的毒性与起始壳聚糖相当,而它们的抗菌活性却更高。通过环氧开环 它们有效地催化脂肪酸和缩水甘油选择性转化为相应的甘油单酯,使人们可以大大简化将反应产物与催化剂分离以回收和再利用的程序。

更新日期:2020-01-26
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