Title

HPLC Resolution of the Enantiomers of Dihydroxyphenylalanine and Selected Salsolinol Derivatives Using Sulfated Beta-Cyclodextrin

Document Type

Article

Publication Date

1-1-2000

Department

Chemistry and Biochemistry

Abstract

D- and L-dihydroxyphenylalanine (D- and L-DOPA) and enantiomers of the tetrahydroisoquinoline alkaloids salsolinol (SAL), 1-carboxysalsolinol (1-CSAL), and cis-3-carboxysalsolinol (3-CSAL) were chromatographed using sulfated beta -cyclodextrin (S-beta -CD) as a chiral selector in mobile phases with conventional reversed-phase ODS columns. S-beta -CD is a very effective chiral, selector for SAL and 3-CSAL, less effective although still useful for resolving D- and L-DOPA, and gives only meager separation of the optical isomers of 1-CSAL. Stoichiometries of the complexes which form between S-beta -CD and SAL enantiomers are 1:1. Interactions between carboxylated substances and S-beta -CD appears to be more complex. Retention of the solutes studied is characterized by favorable negative enthalpy and unfavorable negative entropy changes. Enthalpy changes outweigh entropy values.

Publication Title

Enantiomer

Volume

5

Issue

41337

First Page

377

Last Page

383

This document is currently not available here.

Find in your library

Share

 
COinS