title: Syntheses of chitin-based imprinting polymers and their binding properties for cholesterol.
abstract: A novel chitin derivative, cholesteryl chitin carbonate (Chitin-Chol), was synthesized from chitin and cholesteryl chloroformate. This product was characterized by Fourier transform infrared (FTIR) spectroscopy and solid-state ¹³C nuclear magnetic resonance (¹³C NMR), and was used as a covalently bound template precursor for imprinting cholesterol. After cross-linking with toluene 2,4-diisocyanate, it was efficiently cleaved hydrolytically to afford a guest-binding site accompanying the easy and efficient removal of a sacrificial spacer. The selectivity and efficacy of a chitin-based imprinting polymer for steroid binding were assessed by a chromatographic screening process. The results of binding experiments showed that this molecular imprinting polymer (MIP) has a high binding capacity with cholesterol. The target discrimination towards cholesterol over its close structural analogue suggested that the polymer recognition site was possible on the basis of the inversion of configuration of a single hydroxyl group. In addition, non-covalent imprinting was done using chitin as a precursor and its binding properties for cholesterol were also evaluated.
authors.affiliation: College of Chemistry and Materials Science, Fujian Normal University, Fujian Key Laboratory of Polymer Materials, Fuzhou, China. tongyuejin@yahoo.com.cn
authors.forename: Yuejin
authors.initials: Y
authors.lastname: Tong
authors.forename: Huaimin
authors.initials: H
authors.lastname: Guan
authors.forename: Shaofeng
authors.initials: S
authors.lastname: Wang
authors.forename: Jianwei
authors.initials: J
authors.lastname: Xu
authors.forename: Chaobin
authors.initials: C
authors.lastname: He
mesh_terms: D001665:Binding Sites; D002686:Chitin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D002784:Cholesterol / Q000737:chemistry*; D002788:Cholesterol Esters / Q000138:chemical synthesis*; D003432:Cross-Linking Reagents / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D054802:Molecular Imprinting; D017550:Spectroscopy, Fourier Transform Infrared; D014051:Toluene 2,4-Diisocyanate / Q000737:chemistry
chemical_list: D002788:Cholesterol Esters; D003432:Cross-Linking Reagents; D002686:Chitin; D014051:Toluene 2,4-Diisocyanate; D002784:Cholesterol