Chiral derivatization for separation of racemic amino and thiol drugs by liquid chromatography and capillary electrophoresis

✍ Scribed by Pierre Leroy; Luc Bellucci; Dr. Alain Nicolas

• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: English
• Weight: 565 KB
• Volume: 7
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/chir.530070409

✦ Synopsis

Separation of racemic amino drugs (a-methylbenzeneethanamhe, 6-amino-2-methyl-2-heptanol and 1-amhoethyl-benzenemethanol) and thiol drugs [N-(2mercapto-1-oxopropyl) glycine, 2-mercaptopropanoic acid, and N-acetyl-3-mercaptovaline] has been evaluated after derivatization. ortho-Phthalaldehyde (OPA) and naphthalene-2,3dicarboxaldehyde (NDA) were used with either homochiral thiols (N-acetyl-L-cysteine and N-acetyl-o-penicillamine) or amines [(-)-(lR,2S)-norephedrine, L-phenylalanine, L-tyrosine, and 3-hydroxy-~-tyrosine] as chiral selectors accordmg to the analyte reactive group. The resulting 36 diastereoisomeric derivatives were studied using reversed-phase high-performance liquid chromatography (RP-HPLC) and capillary electrophoresis (CE). Of the CE modes, micellar electrokinetic chromatography (MEKC) using sodium dodecyl sulfate (SDS) as surfactant, P-cyclodextrin (P-CD)-moddied capillary zone electrophoresis (P-CD-CZE), and P-CD-MEKC were applied. Results highlight respective performance of the reagents and separative techniques. All OPA derivatives of racemic amino drugs were resolved either by MEKC or P-CD-MEKC. In the case of racemic thiol drugs, 10 of the 12 OPA derivatives were resolved in P-CD-CZE.