HPLC Resolution of the Enantiomers of Dihydroxyphenylalanine and Selected Salsolinol Derivatives using Sulfated beta-Cyclodextrin
Chemistry and Biochemistry
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.
(2000). HPLC Resolution of the Enantiomers of Dihydroxyphenylalanine and Selected Salsolinol Derivatives using Sulfated beta-Cyclodextrin. Enantiomer, 5(41337), 377-383.
Available at: http://aquila.usm.edu/fac_pubs/9192