高等学校化学学报2018，Vol.39Issue(6)：1164-1171,8.DOI:10.7503/cjcu20170810
羧甲基-β-环糊精手性固定相拆分17种β-内酰胺及其机理
Enantioseparation of Seventeen Kinds of β-Lactams on Carboxymethyl-β-cyclodextrin Chiral Stationary Phase and Research on Enantioseparation Mechanism
周敏 1徐小英 2龙远德1
作者信息
- 1. 中国科学院成都有机化学研究所,成都610041
- 2. 中国科学院大学,北京100049
- 折叠
摘要
Abstract
A reversed phase high performance liquid chromatographic method was developed using carboxymethyl-β-cyclodextrin chiral stationary phase for enantioseparation of seventeen kinds of cis-β-lactams enantiomers. Most of the compounds could get base-line separation. The effects of mobile phase pH, salt type and concentration, as well as mobile phase proportion were discussed. The results showed that ( 0. 10％NH4 Ac+FA ) ( pH= 5. 0 )-MeOH ( 70 : 30, volume ratio ) was the optimum condition for most of chiral compound. Under the optimum condition, the 7 compounds for CA series could get base-line separation except for compound 18CA, the best resolution values for compounds 15CA and 17CA were 1. 71 and 1. 74, respectively. The resolution values for seven EA compounds were between 1. 00 and 1. 50 which was nearly close to base-line separation except for compounds 18EA and 22EA. The resolution values for three BA compounds were close to 1. 00. Structures of analytes also played important role in chiral separation. The results indicated that better resolution could be obtained if the analyte with proper size matching cyclodextrin cavity. Hydrogen bond interaction between the substituents on the cyclodextrin derivative and the analytes and smaller steric hindrance were also good for enantioseparation. Smaller steric hindrance making analytes easily penetrate into cyclodextrin cavity was beneficial to enantioseparation. A tentative chiral recognition mechanism was proposed after a comprehensive analysis of the influencing factors for enantioseparation using compound 15CA as example. Inclusion interaction, hydrogen bond interaction, dipole-dipole interaction and steric hindrance were found to exert synergistic effects on enantioseparation. However, the inclusion interaction between the analytes and the cyclodextrin was the primary role for enantioselective recognition. In comparison with native β-CD CSP , CM-β-CD CSP exhibited enhanced enantioseparation.关键词
羧甲基-β-环糊精/β-内酰胺/手性分离/高效液相色谱Key words
Carboxymethyl-β-cyclodextrin/β-Lactam/Enantioseparation/High performance liquid chromatography分类
化学化工引用本文复制引用
周敏,徐小英,龙远德..羧甲基-β-环糊精手性固定相拆分17种β-内酰胺及其机理[J].高等学校化学学报,2018,39(6):1164-1171,8.
