INDIRECT ENANTIOMERIC SEPARATION OF 2-ARYLPROPIONIC ACIDS AND STRUCTURALLY RELATED-COMPOUNDS BY REVERSED-PHASE HPLC

A reversed-phase high-performance liquid chromatographic method, using an organic modifier-phosphate buffered mobile phase, for the determin ation of the enantiomeric composition of 2-arylpropionic acids and oth er structurally related compounds in microbial media is described. The method is based on the resolution of diastereoisomeric amides formed from the reaction of the arylpropionic acid with either (-)-(S)-alpha- methylbenzylamine or (-)-(S)-1-(naphthen-1-yl)ethylamine in the presen ce of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide HCl and 1-hydroxyb enzotriazole and incorporating an internal standard. The addition of s odium pentanesulphonate to the mobile phase as an ion-pairing agent wa s necessary to remove unreacted amine to avoid rapid column deteriorat ion. The method provides an efficient, rapid and reproducible means of monitoring the microbial chiral inversion of 2-arylpropionic acids an d other structurally related molecules. (C) 1997 Elsevier Science B.V.