P. Leroy et al., CHIRAL DERIVATIZATION FOR SEPARATION OF RACEMIC AMINO AND THIOL DRUGSBY LIQUID-CHROMATOGRAPHY AND CAPILLARY ELECTROPHORESIS, Chirality, 7(4), 1995, pp. 235-242
Separation of racemic amino drugs (alpha-methylbenzeneethanamine, 6-am
ino-2-methyl-2-heptanol and 1-aminoethyl-benzenemethanol) and thiol dr
ugs [N-(2-mercapto-1-oxopropyl) glycine, 2-mercaptopropanoic acid, and
N-acetyl-3-mercaptovaline] has been evaluated after derivatization. o
rtho-Phthalaldehyde (OPA) and naphthalene-2,3-dicarboxaldehyde (NDA) w
ere used with either homochiral thiols (N-acetyl-L-cysteine and N-acet
yl-D-penicillamine) or amines [(-)-(1R, 2S)-norephedrine, L-phenylalan
ine, L-tyrosine, and 3-hydroxy-L-tyrosine] as chiral selectors accordi
ng to the analyte reactive group. The resulting 36 diastereoisomeric d
erivatives were studied using reversed-phase high-performance liquid c
hromatography (RP-HPLC) and capillary electrophoresis (CE). Of the CE
modes, micellar electrokinetic chromatography (MEKC) using sodium dode
cyl sulfate (SDS) as surfactant, beta-cyclodextrin (beta-CD)-modified
capillary zone electrophoresis (beta-CD-CZE), and beta-CD-MEKC were ap
plied. Results highlight respective performance of the reagents and se
parative techniques. All OPA derivatives of racemic amino drugs were r
esolved either by MEKC or beta-CD-MEKC, In the case of racemic thiol d
rugs, 10 of the 12 OPA derivatives were resolved in beta-CD-CZE. (C) 1
995 Wiley-Liss, Inc.