非均匀取代淀粉衍生物手性固定相的制备及其手性识别能力  

Preparation and chiral recognition of heterosubstituted amylose derivatives-based chiral stationary phases

作　　者：王宝存[1] 鲍明辉[1] 林素妃 马婕妤[1] 唐守万[1] WANG Baocun;BAO Minghui;LIN Sufei;MA Jieyu;TANG Shouwan(College of Pharmaceutical and Chemical Engineering,Taizhou University,Taizhou 318000,China)

机构地区：[1]台州学院医药化工学院,浙江台州318000

出　　处：《色谱》2017年第6期572-577,共6页Chinese Journal of Chromatography

基　　金：浙江省大学生科技创新计划(新苗人才计划)项目(2016R430020)~~

摘　　要：通过区域选择性方法制备了两种新型淀粉衍生物,分别为淀粉2-苯甲酸酯-3-(4-甲基苯基氨基甲酸酯)-6-(3,5-二氯苯基氨基甲酸酯)和淀粉2-苯甲酸酯-3-(3,5-二氯苯基氨基甲酸酯)-6-(4-甲基苯基氨基甲酸酯),将二者分别涂覆于氨丙基硅胶后用作液相色谱手性固定相。研究表明:所制备的手性固定相显示出特异的手性识别能力,其手性识别能力明显高于均匀取代淀粉衍生物——淀粉三(3,5-二氯苯基氨基甲酸酯),取代基的性质及在葡萄糖单元上的位置对手性固定相的手性识别能力有较大的影响。一些未在商品化的手性柱Chiralpak AD上得到有效分离的手性化合物在所制备的固定相上得到了更好的分离。所测试的8对对映体在淀粉2-苯甲酸酯-3-(4-甲基苯基氨基甲酸酯)-6-(3,5-二氯苯基氨基甲酸酯)固定相上均得到了分离,因而此固定相的手性识别能力较强,具有潜在的应用价值。Two novel amylose derivatives,namely amylose2-benzoate-3-(4-methylphenylcarbamate)-6-(3,5-dichlorophenylcarbamate)and amylose2-benzoate-3-(3,5-dichlorophenylcarbamate)-6-(4-methylphenylcarbamate),were prepared utilizing a serial regioselective process.After coated onto aminopropyl silica gel,they were utilized as chiral stationary phases(CSPs)for high performance liquid chromatography.Investigations indicated that the CSPs exhibited characteristic chiral recognition and their chiral recognition abilities were much higher than those of amylose tris(3,5-dichlorophenylcarbamate)(AD CPC),a homosubstituted derivative.The nature and position of the substituents at3-,and6-positions of a glucose unit had great influence on the chiral resolution abilities of the amylose derivatives.Some chiral compounds which were not effectively resolved on the commercial column Chiralpak AD were effectively separated on the new CSPs.Moreover,with all the eight tested racemates resolved,amylase2-benzoate-3-(4-methylphenylcarbamate)-6-(3,5-dichlorophenylcarbamate)exhibited relatively high chiral recognition and might be a potential useful CSP.

关 键 词：高效液相色谱 手性固定相 淀粉衍生物 手性分离 多糖 

分 类 号：O658[理学—分析化学]