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

引用本文: 王宝存, 鲍明辉, 林素妃, 马婕妤, 唐守万. 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[J]. 色谱, 2017, 35(6): 572-577. doi: 10.3724/SP.J.1123.2017.02011 shu

Citation: WANG Baocun, BAO Minghui, LIN Sufei, MA Jieyu, TANG Shouwan. Preparation and chiral recognition of heterosubstituted amylose derivatives-based chiral stationary phases[J]. Chinese Journal of Chromatography, 2017, 35(6): 572-577. doi: 10.3724/SP.J.1123.2017.02011 shu

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

台州学院医药化工学院, 浙江台州 318000
基金项目:
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。

关键词:

English

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

College of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, China
Received Date: 13 February 2017
Fund Project:
Zhejiang College Students' Science and Technology Innovation Project (Xinmiao Talents Program) (No. 2016R430020).

Abstract: Two novel amylose derivatives, namely amylose 2-benzoate-3-(4-methylphenylcarbamate)-6-(3,5-dichlorophenylcarbamate) and amylose 2-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) (ADCPC), a homosubstituted derivative. The nature and position of the substituents at 3-, and 6-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, amylose 2-benzoate-3-(4-methylphenylcarbamate)-6-(3,5-dichlorophenylcarbamate) exhibited relatively high chiral recognition and might be a potential useful CSP.

Key words:

high performance liquid chromatography (HPLC)
/ chiral stationary phase (CSP)
/ amylose derivative
/ chiral separation
/ polysaccharide

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沈阳化工大学材料科学与工程学院沈阳 110142

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

English

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

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

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

English

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

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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