Zhao Jie, Lu Xiaohong, Wang Yong, Lv Jie
Department of Chemistry, School of Science, Tianjin University Tianjin 300072.
Department of Chemistry, School of Science, Tianjin University Tianjin 300072; Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China.
J Chromatogr A. 2015 Feb 13;1381:253-9. doi: 10.1016/j.chroma.2015.01.008. Epub 2015 Jan 14.
This paper reports an effective approach for the fabrication of a novel hybrid bilayer cyclodextrin (CD) chiral stationary phase (CSP), where native and perphenylcarbamoylated-β-CD were successively immobilized onto silica surface via a two-step click approach to form a bilayer CD structure. By decorating the bulky phenylcarbamoylated CD onto the unmodified CD silica, the CSP can provide multiple interaction sites such as H-bonding (-OH, C=O, -NH-), steric effects, π-π, dipole-dipole and inclusion complexation interactions, which help to broaden the CSP's enantioselectivity profile and enhance the enantioselectivity to some specific analytes. A group of enantiomer pairs such as isoxazolines, bendroflumethiazide, indoprofen, diperodon, fenoterol, atropine, styrene oxide and dansyl amino acids can be baseline or partially separated on the current CSP under reversed phase high performance liquid chromatography (RP-HPLC). The selectivity and resolution of 4NPh-OPr reached 5.25 and 13.97, which is an exciting achievement for the enantioseparations by CD CSPs.
本文报道了一种制备新型混合双层环糊精（CD）手性固定相（CSP）的有效方法，其中天然β-环糊精和全苯基氨基甲酰化-β-环糊精通过两步点击法依次固定在硅胶表面，形成双层CD结构。通过在未修饰的CD硅胶上修饰体积较大的苯基氨基甲酰化CD，该CSP可以提供多种相互作用位点，如氢键（-OH、C=O、-NH-）、空间效应、π-π、偶极-偶极和包合络合相互作用，这有助于拓宽CSP的对映体选择性范围，并增强对某些特定分析物的对映体选择性。在反相高效液相色谱（RP-HPLC）条件下，一组对映体对，如异恶唑啉、苄氟噻嗪、吲哚美辛、地哌冬、非诺特罗、阿托品、环氧苯乙烷和丹磺酰氨基酸，在当前的CSP上可以实现基线分离或部分分离。4NPh-OPr的选择性和分离度分别达到5.25和13.97，这对于CD CSPs的对映体分离来说是一项令人振奋的成果。
