Synthesis and application of chitosan thiourea derivatives as chiral stationary phases in HPLC.

Hongzhong Deng, Xuepeng Wu, Lili Zhang, Jun Shen, Yingjie Qiao, Xiaodong Wang, Chengying Bai, Ting Zheng, Yoshio Okamoto

Carbohydrate polymers 2022 Nov 15

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Chitosan 2-thiourea derivatives with various substituents, including 3-(methylthio)propyl, phenyl, octyl and ethoxycarbonyl, at the 2-position of the glucosamine skeleton were prepared via isothiocyanates with the above substituents. The obtained chitosan 2-thiourea derivatives without ethoxycarbonyl were then esterified to develop a new series of chitosan 2-thiourea-3,6-diphenylcarbamate derivatives. The enantioseparation properties of the obtained chitosan derivatives were examined by high-performance liquid chromatography (HPLC). These results demonstrated that these chitosan 2-[3-(methylthio)propylthiourea]-3,6-diphenylcarbamate derivatives showed attractive chiral recognition abilities, especially for dihydropyridine calcium antagonist racemates. This result was probably attributed to the fact that the 2-thiourea substituents of this series of chitosan derivatives, as well as the 3,6-phenylcarbamate substituents, provided more favorable sites, which evidently enhanced the interactions between the enantiomers and the chitosan derivatives. The mechanism involved in the enantioseparation of the chitosan 2-[3-(methylthio)propylthiourea]-3,6-diphenylcarbamate derivatives was further discussed by molecular docking simulation. Copyright © 2022 Elsevier Ltd. All rights reserved.

Citation

Hongzhong Deng, Xuepeng Wu, Lili Zhang, Jun Shen, Yingjie Qiao, Xiaodong Wang, Chengying Bai, Ting Zheng, Yoshio Okamoto. Synthesis and application of chitosan thiourea derivatives as chiral stationary phases in HPLC. Carbohydrate polymers. 2022 Nov 15;296:119888