Relevance and bio-catalytic strategies for the kinetic resolution of ketoprofen towards dexketoprofen

Abstract

This review presents the most relevant investigations concerning the biocatalytic kinetic resolution of racemic ketoprofen to dexketoprofen for the last 22 years. The advantages related to the administration of the dex-enantiomer in terms of human health, the so called “chiral switch” in the pharmaceutical industry and the sustainability of biotransformations have been the driving forces to develop innovative technology to obtain dexketoprofen. In particular, the kinetic resolution of racemic ketoprofen through enantiomeric esterification and hydrolysis using lipases as biocatalysts are thoroughly revised and commented upon. In this context, the biocatalysts, acyl-acceptors (alcohols), reaction conditions, conversion, enantiomeric excess, and enantiomeric ratio among others are discussed. Moreover, the investigations concerning scaling up processes in order to obtain an optically pure enantiomer of the profen are presented. Finally, some guidelines about perspectives of the technology and research opportunities are given.

Keywords:

• Ketoprofen
• dexketoprofen
• kinetic resolution
• esterification
• hydrolysis
• lipases
• biocatalysis

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

The authors acknowledge the financial support provided by Consejo Nacional de Investigaciones Científicas y Técnicas CONICET of Argentina and National University of La Plata U.N.L.P.