Use of hydroxypropyl- and hydroxyethyl-derivatized beta-cyclodextrins for the thin-layer chromatographic separation of enantiomers and diastereomers.
Partially substituted hydroxypropyl-beta-cyclodextrin and hydroxyethyl-beta-cyclodextrin proved to be effective chiral mobile phase additives (CMAs) for the thin-layer chromatographic (TLC) resolution of racemic benzyl-2-oxazolidinone, 5-(4-methyl-phenyl)-5-phenylhydantoin, mephenytoin and several dansyl and beta-naphthylamide amino acids. Several diastereomeric compounds including steroid epimers and alkaloids were separated as well. The derivatized beta-cyclodextrins tended to be much more soluble in water and hydro-organic solvents than native beta-cyclodextrin. Their chromatographic selectivity also was somewhat different. The use of CMAs in TLC is a potentially useful and powerful method that has not been considered adequately. The relative lack of chiral stationary phases available in planar format makes the use of CMAs particularly attractive.
Armstrong
D W
DW
Department of Chemistry, University of Missouri-Rolla 65401-0249.
Faulkner
J R
JR
Han
S M
SM
D000073738:2-Hydroxypropyl-beta-cyclodextrin; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D003505:Cyclodextrins; D003619:Dansyl Compounds; D003912:Dextrins; D008970:Molecular Weight; D012995:Solubility; D013213:Starch; D013237:Stereoisomerism; D047392:beta-Cyclodextrins
D003505:Cyclodextrins; D003619:Dansyl Compounds; D003912:Dextrins; D047392:beta-Cyclodextrins; D000073738:2-Hydroxypropyl-beta-cyclodextrin; D013213:Starch; C059250:2-hydroxyethyl-beta-cyclodextrin; C031215:betadex