通过点击化学方式对单叠氮环糊精进行衍生,引入具备不同作用位点的功能化基团,对环糊精手性分离性能进行调控。首先通过醚键将单叠氮环糊精接枝到硅胶表面进一步通过Cu(Ⅰ)催化的1,3-偶极环加成反应(点击化学)在环糊精小口端分别引入叔丁基、苯基、酯基和羟基基团,构建了4种新型环糊精手性固定相并通过红外光谱和元素分析对其进行了结构表征。通过高效液相色谱反相分离模式实现了异嗯唑啉和丹磺酰氨基酸共16种对映体的手性拆分。酯基功能化的环糊精手性固定相对多数异嗯唑啉类有良好的拆分效果,其中,2-氯苯基-异嗯唑(2ClPh-OPr)分离度可达1.62。丹磺酰氨基酸类最佳分离pH值为5.0,叔丁基功能化固定相具有最好的分离效果,大部分样品可实现基线分离(Rs〉1.5)。
This work fabricates four novel chiral stationary phases(CSPs) by tuning the functionality on cyclodextrin(CD) small mouth via click chemistry.Mono-6-deoxy-azido CD was anchored onto silica surface via ether linkage,followed by introducing tert-butyl,phenyl,ester and hydroxyl groups to the azido CD silica respectively.The as-prepared four novel CD CSPs were characterized by FTIR and elemental analysis.16 enantiomer pairs including isoxazolines and dansyl amino acids could be baseline or partially separated on the current CD CSPs under reversed-phase separation mode.Ester functionalized CD CSP exhibited good chiral recognition towards isoxazolines and the resolution of 2-chlorphenyl-isoxazole(2ClPh-OPr) reached 1.62.The optimum pH for the separation of dansyl amino acids was 5.0.Among the prepared CSPs,Tert-butyl functionalized CD CSP had the best enantioseparation performance towards dansyl amino acids with most of the analytes baseline separated(Rs〉1.5).