Enantioseparation of Flavanoids, Isoxazolines, Dansyl Amino Acids and β-Blockers on Native and Phenylcarbamoylated α, β and γ-Cyclodextrin Chiral Stationary Phases

Abstract

In this study, a series of native and p‐methylphenylcarbamoylated cyclodextrin chiral stationary phases (CD‐CSPs) were developed based on α, β and γ‐cyclodextrin via ether linkage. The as‐prepared CSPs were characterized by FTIR, solid‐state C13 NMR, thermogravimetric analysis and elemental analysis. Their enantioseparation properties were comprehensively investigated by using high performance liquid chromatography (HPLC) with various racemates including flavanoids, isoxazolines, dansyl amino acids and β‐blockers. The effects of CD cavity size and CD functionalities on the enantioseparation results were evaluated in detail. The correlation between analyte structures and their chiral resolution were also investigated. A reference chart has been proposed for quick choice of CD‐CSPs for enantioseparation of specific racemates.

Progress in the Enantioseparation of β-Blockers by Chromatographic Methods

“…Among all these derivatives, the most widely used and effective CSPs are aromatic derivatized CD, especially phenylcarbamoylated CDs, which can produce more interactions such as π-π interaction, dipole-dipole interaction and hydrogen bonds because of the introduction of aromatic rings, “N-H” bonds and “C=O” bonds. Jin et al [ 67 ] synthesized phenylcarbamoylated α, β and γ-cyclodextrin chiral stationary phases and it turns out that the above CSPs have better enantioselectivity towards β-blockers than native CDs. Wang et al [ 42 , 68 ] prepared two CSPs by immobilization of phenylcarbamoylated β-CDs onto alkynyl modified silica via “click” chemistry and successfully resolved β-blockers.…”