新型正电型β-环糊精衍生物的合成及其毛细管电色谱开管柱的应用
用于分离手性化合物的研究中，是近年来 β-环糊精衍生物的研究热点。本论文制
备了两种兼有铵基及咪唑鎓基的正电型环糊精衍生物，一种为双取代双正电中心
的 6A-铵基-6C-乙基咪唑鎓基-β-环糊精；另一种为单取代双正电中心的 6A-铵基丁
基咪唑鎓基-β-环糊精，对酸性化合物及氨基酸类化合物均有良好的拆分能力。所
制得的产物通过熔点测试、1HNMR、13CNMR、FT-IR等进行表征。同时利用所制
备的第二种β-环糊精衍生物，作为手性固定相，用于制备新型毛细管手性开管柱，
以用于毛细管电色谱手性分离中。5145
关键词 手性分离 β-环糊精衍生物 毛细管电泳 开管柱 毛细管电色谱
Title Synthesis of novel cationic β-cyclodextrin
derivatives and their applications in open tubular
column capillary electrochromatography
Abstract
In recent years development of positively charged cyclodextrin (CD) has
become one of the most important topics in the field of cyclodextrin
chemistry. They have showed good chiral separation ability for anionic
enantiomers and Dns-amino acids. This thesis mainly focuses on the
synthesis of two novel positively charged β-cyclodextrins. The first
positively charged β-cyclodextrin is disubstituted
6A
-ammonium-6C
-ethylimidazolium-β-cyclodextrin with two positively
charged centers, and the second one is mono-substituted
6A
-ammonium-butyl-imidazolium-6A
-deoxyl-β-cyclodextrin, also with two
positively charged centers in the CD rim. These twoβ-cyclodextrin
derivatives possessed both ammonium and imidazolium group, with whied they
exhibited excellent chiral separation for both Dns-amino acid and acidic
racemates. All reaction intermediate compounds and final products were
carefully characterized and structurally confirmed by melting point
measurement、 1
HNMR、13
CNMR and FT-IR analyses. The second β-cyclodextrin
derivative was further employed for the preparation of chiral stationary
phase in open-tubular column for capillary electrochromatography.
Keywords Chiral separation β-Cyclodextrin derivates Capillary
electrophoresis Open-tubular column Capillary electrochromatography 目 次
1 绪论 .. 1
1.1 手性药物. 1
1.1.1 手性及手性药物 . 1
1.1.2 手性药物的拆分技术 .. 2
1.2 毛细管电泳在药物手性拆分中的应用 .. 2
1.2.1 毛细管电泳技术简介 .. 2
1.2.2 毛细管电泳的基本原理.. 3
1.2.3 毛细管电泳的常用手性拆分剂 .. 6
1.3 环糊精及其衍生物 7
1.3.1 环糊精 . 7
1.3.2 环糊精衍生物 .. 8
1.4 论文研究内容及创新点 .. 10
2 6A
-铵基-6C
-乙基咪唑鎓基-β-环糊精的制备. 11
2.1 前言 11
2.2 实验 12
2.2.1 实验试剂 .. 12