Enzyme‐catalyzed Asymmetric Synthesis

Gonzalo, Gonzalo; Alcántara, Andrés R.

doi:10.1002/9781119736424.ch14

Cited by 2 publications

(1 citation statement)

References 137 publications

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“…Very recently, Zdun et al [17] have reported the use of methyl and ethyl orthoesters (orthoacetates and orthobenzoates, R 3 = Me or Ph) for the stereoselective esterification of different profens (ibuprofen, ketoprofen, naproxen, flurbiprofen), using Novozym ® 435, a commercial CALB immobilized on polymethylmethacrylate [64]. In all cases, the enantioselectivity reported was modest, as lipases are more effective in the chiral discrimination of substrates possessing the stereocentre in the alcohol rather than in the acid moiety, as occurs with profens [65]. For esterification of this acids (Figure 1A), it is established that the addition of a relatively polar cosolvent along the main solvent constitutes another approach to optimize the enantioselectivity of lipases in both hydrolysis and esterification reactions with profens [16].…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2023

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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.

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Section: Introductionmentioning

confidence: 99%

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

et al. 2023

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Microwave-Assisted Enzymatic Reactions toward Medicinally Active Heterocycles

Das,

Banik

2024

DDC

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Microwaves in the presence of enzymes can contribute to the preparation of a variety of medicinally active compounds. Microwave-induced enzymatic reactions are influenced by variables such as frequency, field strength, waveform, duration, and modulation. The activation of enzymes under microwave irradiation allows the study of simple and complex reactions that have never before been reported under these conditions. By combining enzyme catalysis with microwave technology and solvent-free chemical reactions, it is possible to prepare drug-related molecules. This review presents the most interesting microwave reactions performed by enzymes toward medicinally active molecules.

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Enzyme‐catalyzed Asymmetric Synthesis

Cited by 2 publications

References 137 publications

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

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

Microwave-Assisted Enzymatic Reactions toward Medicinally Active Heterocycles

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