HPLC resolution of the enantiomers of dihydroxyphenylalanine and selected salsolinol derivatives using sulfated beta-cyclodextrin.
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.
McMurtrey
K
K
Department of Chemistry and Biochemistry, University of Southern Mississippi, Hattiesburg, MS 39406, USA.
Strawbridge
C
C
McCoy
J
J
D000978:Antiparkinson Agents / Q000737:chemistry / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D003505:Cyclodextrins / Q000737:chemistry*; D004295:Dihydroxyphenylalanine / Q000737:chemistry / Q000302:isolation & purification*; D007546:Isoquinolines / Q000737:chemistry / Q000302:isolation & purification*; D013237:Stereoisomerism; D013464:Sulfuric Acids / Q000737:chemistry; D013816:Thermodynamics; D047392:beta-Cyclodextrins
D000978:Antiparkinson Agents; D003505:Cyclodextrins; D007546:Isoquinolines; D013464:Sulfuric Acids; D047392:beta-Cyclodextrins; D004295:Dihydroxyphenylalanine; C036617:salsolinol; C031215:betadex