点击化学制备新型手性配体交换色谱固定相  

Preparation of A Novel Chiral Ligand Exchange Chromatographic Stationary Phase by Click Chemistry

作　　者：付春梅[1] 石宏宇[2] 李章万[1] 钱广生[1] 

机构地区：[1]四川大学华西药学院,成都610041 [2]北京东西分析仪器有限公司,北京102308

出　　处：《分析化学》2010年第7期1011-1014,共4页Chinese Journal of Analytical Chemistry

摘　　要：采用点击化学反应制备了一种新型L-脯氨酰胺衍生物键合手性配体交换色谱固定相。硅胶与γ-氯丙基三乙氧基硅烷反应后,再与叠氮化钠反应制备得到叠氮化硅胶。在甲醇溶液中,以溴化亚铜为催化剂,叠氮化硅胶与合成的手性选择子N-炔丙基脯氨酰胺,室温反应48h,而键合上手性官能团。手性选择子的键合量达0.47mmol/g,操作简单,反应条件温和。制备的手性固定相以0.2mmol/LCu(Ac)2水溶液为流动相,在配体交换模式下拆分了8种D,L-氨基酸,对映体选择因子α在1.14～2.42之间。手性分离能力和稳定性研究表明,点击化学在手性配体交换色谱固定相的制备中具有极大潜力。Click chemistry was applied to immobilize L-prolinamide derivative onto azide-modified silica gel to prepare a novel chiral stationary phase for ligand exchange chromatography （Click-CSP）.Azide functionalities were introduced onto the silica gel by reacting γ-chloropropyltriethoxysilane with silica gel,and then the obtained product was reacted with sodium azide.The azide-modified silica gel reacted with N-propargyl prolinamide chiral selector prepared in methanol at room temperature for 48 h in the presence of copper（Ⅰ） bromide to give a novel chiral stationary phase for ligand exchange chromatography.The developed protocol combines the benefits of operational simplicity,exceptionally mild conditions and high surface loadings up to 0.47 mmol/g.The enantiomeric separation of some D,L-amino acids were achieved on the synthesized chiral ligand exchange chromatographic stationary phase using 0.2 mmol/L Cu（Ac）2 solution as mobile phase at column temperature of 40 ℃ with selectivity factors α from 1.14 to 2.42.The chromatographic resolutions of some D,L-amino acids and the stability of the Click-CSP firmly illustrate the potential of click chemistry for preparation chiral stationary phase for ligand exchange chromatography.

关 键 词：点击化学 手性配体交换色谱固定相 L-脯氨酰胺 D L-氨基酸 

分 类 号：O657.7[理学—分析化学]