On the Use of Orthoformates as an Efficient Approach to Enhance the Enzymatic Enantioselective Synthesis of (S)-Ibuprofen

Khiari, Oussama; Bouzemi, Nassima; Sánchez Montero, José; Alcántara León, Andrés Rafael

On the Use of Orthoformates as an Efficient Approach to Enhance the Enzymatic Enantioselective Synthesis of (S)-Ibuprofen

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catalysts-13-00251-v3.pdf (1.79 MB)

Official URL

https://doi.org/10.3390/catal13020251

Publication date

2023

Authors

Khiari, Oussama

Bouzemi, Nassima

Sánchez Montero, José

Alcántara León, Andrés Rafael

Advisors (or tutors)

Sánchez Montero, José

Alcántara León, Andrés Rafael

Publisher

MDPI

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URI

https://hdl.handle.net/20.500.14352/92528

Citation

Khiari, O.; Bouzemi, N.; Sánchez-Montero, J.M.; Alcántara, A.R. On the Use of Orthoformates as an Efficient Approach to Enhance the Enzymatic Enantioselective Synthesis of (S)-Ibuprofen. Catalysts 2023, 13, 251. https://doi.org/10.3390/catal13020251

Abstract

In this paper, we describe the effectiveness of the combination between an organic solvent system mixture with orthoformates with different chain sizes from one to four carbon atoms. These orthoesters have been used as a “water trapper/alcohol releaser molecule” to reach a notable improvement in enantioselectivity and enantiomeric excess of our target compound, (S)-2-(4-isobutylphenyl)propanoic acid (ibuprofen eutomer), during the enzymatic kinetic resolution of rac-ibuprofen using immobilized lipase B of Candida antarctica as a biocatalyst. At the same time, one of the great problems of biocatalysis in organic media has been solved by eliminating excess water in the medium that allows the reversibility of the reaction. Following the optimization of the reaction conditions, an increase in enantiomeric excess and enantioselectivity was reached by using these acyl donors in the presence of a cosolvent.