胆碱磷酰化偶联壳聚糖仿生衍生物的合成及表征

Synthesis and Characterization of Biomimetic Choline-Chitosan Derivatives with a Phosphoramide Linkage

采用Antherton-Todd反应合成了两种胆碱磷酰化偶联壳聚糖衍生物——带双正电荷的N-二胆碱磷酰化偶联壳聚糖(N-PC+Cs)和两性的N-磷酸胆碱磷酰化偶联壳聚糖(N-PCCs),并用核磁共振波谱(NMR)和红外光谱(IR)表征其化学结构。由1H-NMR谱得到N-PC+Cs的取代度为30.9%,N-PCCs的取代度为32.6%。X射线衍射谱(XRD)和热分析的结果表明,与壳聚糖相比,N-PC+Cs和N-PCCs的结晶性和热稳定性都显著降低。水溶性试验表明,两种仿生衍生物在中性水溶液中都表现出良好的溶解性,有望用于药物/基因传输系统载体。

Two kinds of biomimetic chitosan derivatives with a phosphoramide linkage between glucosamine and choline were successfully synthesized through Atherton-Todd reaction under the mild conditions,including double positively-charged phosphorylcholine（PC） bound chitoan（N-PC＋Cs） and zwitterionic phosphorylcholine bound chitosan（N-PCCs）.Their chemical structures were confirmed by nuclear magnetic resonance（NMR） and Fourier transform infrared spectroscopy（FT-IR）.According to the 1H-NMR spectras,the degree of substitution（DS） is 30.9% and 32.6% for N-PC＋Cs and N-PCCs,respectively.Their physical form,water solubility and thermal properties were also investigated by X-ray diffraction （XRD）,UV-Vis spectra and differential scanning calorimetry（DSC）.The results indicate that both biomimetic chitosan derivatives with decreased crystallization and thermal stability show good soluble in the neutral aqueous solutions,which could be used in drug/gene delivery systems.