Direct enantioselective HPLC monitoring of lipase‐catalyzed kinetic resolution of flurbiprofen

Ghanem, Ashraf

doi:10.1002/chir.20798

Cited by 15 publications

(11 citation statements)

References 34 publications

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“…ee p = R -S R + S x 100 (6) The concentration (c) is also expressed in percentage, using (5) and (6) for calculation of conversion equations.…”

Section: Analysis Of Ibuprofenmentioning

confidence: 99%

“…Furthermore, it should be considered, that lipases tolerate a great number of non-natural substrates, are stable and active in organic solvents and necessitate no cofactors. Based on the previous reports, it seems to be obvious, that use of these enzymes as biocatalysts in the industry will be continuously increasing due to their high activity and low price [6][7][8][9].…”

Section: Introductionmentioning

confidence: 99%

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Application of Lipases from Candida rugosa in the Enantioselective Esterification of (R,S)-Ibuprofen

Siódmiak¹,

Ruminski²,

Marszałł³

2012

COC

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Three commercially available lipases from Candida rugosa (OF and MY from Meito Sangyo Co., and CRL from Sigma-Aldrich Co.) were used for the enantioselective esterification reaction of (R,S)-ibuprofen with 1-propanol and 2-propanol in saturated cyclohexane as reaction medium. All tested lipases preferentially catalysed the esterification of the S-enantiomer of ibuprofen. However, each one of the analysed lipases demonstrated differences in the catalytic activity. Lipase OF showed the highest conversion degree, and the best enantioselectivity was observed for MY and CRL lipases. The influence of temperature, reaction time and addition of N,N'dicyclohexylcarbodiimide (DCC) on the enantioselectivity and on the conversion degree in the enzymatic esterification was studied and the optimal condition for enantioselective esterification was evaluated. Moreover, the application of new commercial cellulose-based tris(3,5-dimethylphenylcarbamate) HPLC chiral column was demonstrated for effective separation, qualification and quantification of both substrates and products within one chromatographic analysis.

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“…ee p = R -S R + S x 100 (6) The concentration (c) is also expressed in percentage, using (5) and (6) for calculation of conversion equations.…”

Section: Analysis Of Ibuprofenmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Application of Lipases from Candida rugosa in the Enantioselective Esterification of (R,S)-Ibuprofen

Siódmiak¹,

Ruminski²,

Marszałł³

2012

COC

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“…Candida antarctica lipase is commercially available as a free and immobilized form. Additionally, what is important from a pharmaceutical point of view, CALB shows a stereopreference towards the ( R )‐enantiomer in organic solvents which was reported and proven in many studies . However, in some cases the enantiopreference of CALB is towards the ( S )‐enantiomer, which is dependent on the support on which the enzyme is immobilized as well as the reaction medium .…”

Section: Introductionmentioning

confidence: 96%

“…Ghanem conducted the kinetic resolution of ( R , S )‐flurbiprofen with the use of Candida antarctica lipase as a biocatalyst and n ‐butanol as a nucleophilic agent (Fig. ).…”

Section: Introductionmentioning

confidence: 99%

“…The use of acetonitrile as a standard reaction medium in kinetic resolution of ( R,S )‐flurbiprofen allowed to obtain the product with a high rate of enantiomeric purity, ee p = 72.3% and ee p = 60.4%, respectively, for the Novozym 435 and Novozym 525. Following the procedure reported by Ghanem, Tamborini et al performed the kinetic resolution of ( R , S )‐flurbiprofen with CALB. After 6 h of reaction they were able to obtain the product with an enantiomeric excess ee p = 86% and the conversion was c = 38%.…”

Section: Introductionmentioning

confidence: 99%

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Kinetic Resolution of Profens by EnantioselectiveEsterification Catalyzed by Candida antarctica and Candida rugosa Lipases

2014

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Profens (2-arylpropionic acids) are known as one of the major nonsteroidal antiinflammatory drugs (NSAIDs) used in the treatment of inflammation associated with tissue injury. The inflammatory activity of profens is mainly due to their (S)-enantiomer, whereas they are commercially available not only as pure enantiomers, but as racemates as well. There are several methods widely used in order to obtain enantiomerically pure compounds, however, the kinetic resolution with the application of lipases as biocatalysts may have an added advantage in the production of optically pure active pharmaceutical ingredients, such as milder reaction conditions, reduced energy requirements, and production costs. The aim of this study was to compare the results described in the literature in the case of the influence of reaction medium, alcohol moiety, and reaction temperature on the catalytic activity of lipases from Candida antarctica and Candida rugosa.

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Lipase Enzymes for Sustainable Synthesis of Pharmaceuticals and Chiral Organic Building Blocks

Khanra,

Ravichandiran,

Swain

2024

Advanced Sustainable Systems

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Biocatalysis is a green and sustainable process for synthesizing chiral organic building blocks and active pharmaceutical ingredients (API). United Nations' Sustainable Development Goals 2030 advocates using green, sustainable, recyclable chemicals by industries to reduce environmental pollution. Pharmaceutical companies are adopting biocatalysis technologies for manufacturing chiral active pharmaceutical ingredients. The lipase‐catalyzed kinetic and dynamic‐kinetic resolution method is a pharmaceutically accepted process for manufacturing chiral API. This review describes the reported methods for synthesizing chiral API/KSM (Key Starting Material) molecules using lipase enzymes over the last ten years.

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Direct enantioselective HPLC monitoring of lipase‐catalyzed kinetic resolution of flurbiprofen

Cited by 15 publications

References 34 publications

Application of Lipases from Candida rugosa in the Enantioselective Esterification of (R,S)-Ibuprofen

Application of Lipases from Candida rugosa in the Enantioselective Esterification of (R,S)-Ibuprofen

Kinetic Resolution of Profens by EnantioselectiveEsterification Catalyzed by Candida antarctica and Candida rugosa Lipases

Lipase Enzymes for Sustainable Synthesis of Pharmaceuticals and Chiral Organic Building Blocks

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