Enantiomeric resolution of derivatives of α-aminophosphonic and α-aminophosphinic acids by high-performance liquid chromatography and capillary electrophoresis

Abstract

Resolution of chiral α-aminophosphonic and α-aminophosphinic acid esters analogous to phenylalanine or phenylglycine is achieved by HPLC with chiral cellulose or amylose phases. Resolution of the corresponding racemic acids is successfully performed by capillary electrophoresis. For derivatives analogous to phenylalanine, enantioselectivity of both analytical methods is depending on functional groups at the ring, the groups at the phosphorus atom as well as the structure of protecting groups. Suitable resolution conditions were found for all aminophosphonic and aminophosphinic acid derivatives either at HPLC by variation of chiral stationary phases and the eluent or at CE by using different β-cyclodextrin derivatives at specific conditions.