Thin-layer chromatographic and polarimetric investigation of the oscillatory in-vitro chiral inversion ofS-(+)-ketoprofen

Abstract

Summary Our earlier thin-layer chromatographic and polarimetric investigations enabled discovery of the spontaneous in-vitro oscillatory chiral inversion of the profen drugs S-(+)-ibuprofen, S-(+)-naproxen, and S-(+) and R-(–)-flurbiprofen, etc., and then of the α-amino acids Lphenylalanine, L-alanine, and L-tyrosine. In those investigations, thin-layer chromatography convincingly demonstrated its potential as a flexible and handy tool in the service of physical organic chemistry in general and investigation of organic reaction mechanisms in particular. Later – largely on the basis of thin-layer chromatographic evidence – we proposed a reaction–diffusion model that may provide the core of a mechanistic understanding of the spontaneous oscillatory in-vitro chiral inversion of profens and α-amino acids. In this study, we present thin-layer chromatographic and polarimetric evidence of the analogous process of the oscillatory chiral in-vitro inversion of S-(+)-ketoprofen, which is meant to expand an already existing database, mostly originating from our laboratory and documenting the universal nature of this process with α-substituted chiral propionic acid derivatives (in the first instance, profen drugs and α-amino acids).