PREPARATION AND CHROMATOGRAPHIC CHARACTERISTICS OF A CHIRAL-RECOGNIZING PERPHENYLATED CYCLODEXTRIN COLUMN

摘要

A novel bifunctional chiral recognizing column (PhCD column) was prepared by immobilizing, on silica gel, beta-cyclodextrin (CD) which was perphenylated through the reaction of phenyl isocyanate. Using several enantiomeric compounds, chiral recognition by CD was determined to be maintained in a PhCD column. The chromatographic characteristics of a PhCD column were compared with those of a column (CD column) bound with underivatized CD, and the following properties were found. For polyaromatic compounds and alkylbenzene derivatives, hydrophobic interaction is predominant, and for phenylalkyl alcohols and amines whose enantiomers are hard to recognize on a CD column, specific enantioselectivity was exhibited under the effects of the chemical structure around the chiral centre of the solutes. This added function is possibly an induced fit caused by the phenyl cluster on the CD openings. Using these properties, various enantiomeric drugs, in particular beta-blockers (amino alcohols), which are hardly separated on conventional chiral separation columns, could be separated. [References: 10]