Urea bonded cyclodextrin derivatives onto silica for chiral HPLC

Abstract

Several structurally well-defined perfunctionalised cyclodextrin chiral stationary phases (CD CSPs) for high performance liquid chromatography have been successfully prepared by immobilisation of perfunctionalised cyclodextrins on silica through urea linkage(s) using the Staudinger reaction. These CSPs show high chiral recognition efficiency and are utilised in the resolution of various types of racemic compounds. This paper reviews the development of sixteen perfunctionalised cyclodextrin-based CSPs, their preparation, and their application to enantioseparation of seventy-seven racemic compounds under a range of separation conditions.

Efficient and Versatile Modification of the Secondary Face of Cyclodextrins through Copper‐Catalyzed Huisgen 1,3‐Dipolar Cycloaddition

“…[30] Introduction of functional groups is the most effective strategy to obtain CDs with improved properties. Because the primary hydroxy groups are the most reactive, methods to selectively modify the primary face of CDs are well-established in the literature.…”

Effects of Temperature and Mobile Phase Condition on Chiral Recognition of Poly(l-phenylalanine) Chiral Stationary Phase

“…To date, CSPs with several chiral selectors, such as cyclodextrins [1], macrocyclic antibiotics [2], polysaccharide derivatives [3], modified amino acids [4], proteins [5] and cinchona alkaloids [6], have been reported and some of them are commercially available. We recently developed new series of the CSPs having poly(L-Phe) peptide selector and successfully applied for chiral separations of some pharmaceuticals in reversed-and normal-phase modes [7,8].…”

Investigation of Novel Peptide Chiral Selectors Prepared by Solid-Phase Synthesis with a tert-Butoxycarbonyl Amino Acid

“…The design and development of CSPs has attracted much attention for a number of years. To date, CSPs with several chiral selectors, such as cyclodextrins [1], macrocyclic antibiotics [2], polysaccharide derivatives [3], modified amino acids [4,5], proteins [6] and cinchona alkaloids [7], have been reported and some of them are commercially available. Since CSPs with a protein chiral selector have excellent enantioselectivity, a peptide chiral selector would seem to offer promise.…”