Sulfobutyl Ether .beta.-Cyclodextrin as a Chiral Discriminator for Use with Capillary Electrophoresis

Abstract

The first applications of a novel polyanionic derivative of (S-cycIodextrin (/3-CD), sulfobutyl ether ß-CO (ß-CO-SBE(IV)), as a stereoisomer selector in capillary electrophoresis are described. Separations were developed for one and two chiral molecules, including (±)-ephedrine, (±)pseudoephedrine, and several structurally related compounds.The separations achieved were found to be superior to those possible with neutral selectors such as ß-CO or heptakis(2,6dimethyl)-/8-CD. Base line separation of the four stereoisomers of (±)-ephedrine and (±)-pseudoephedrine was achieved in a single run with /S-CD-SBE(IV). Aspects regarding structural specificity, binding magnitude, and the utility of having a stereoisomer selector with a large countercurrent mobility are discussed.

A spectrophotometric and NMR study on the formation of an inclusion complex between dopamine and a sulfonated cyclodextrin host

“…It has been suggested that the anionic CDs provide maximum separation by migrating in opposite directions to the analyte [15]. In particular, sulfated and highly sulfated b-CDs have been used with some success [12][13][14][15].…”

Cyclodextrin‐modified capillary electrophoresis for achiral and chiral separation of ergostane and lanostane compounds extracted from the fruiting body of Antrodia camphorata

“…The peak assignment of this chiral pair was not possible due to the lack of commercial standards. Chiral resolution of neutral and cationic species can be enhanced by addition of anionic SBCD [25]. Apparently, a combination of the two CDs was necessary to create a chiral environment that modified the physicochemical properties of the two optical isomers, transforming enantiomers to diastereoisomers.…”

Advances in capillary electrophoresis

“…In comparison with chiral HPLC separations capillary electrophoresis offers a more straightforward separations which are more easy to interpret as long as the interactions allowing for stereoisomer separations occur directly with a chiral selector added to the background electrolyte. The most common chiral selectors are optically active micelles [142], cyclodextrins [143][144][145][146], derivatized cyclodextrins [147,148], ligand exchangers [149], macrocyclic antibiotics [150,151], polymeric stereoselective modifiers [152], glycosaminoglycans [153], and crown ethers [154][155][156][157][158][159]. In some instances the chiral selector has been bound to the capillary wall or included into a gel [140].…”