Catalytic and molecular insights of the esterification of ibuprofen and ketoprofen with glycerol

Toledo, María Victoria; José, Carla; Suster, Carlos Rafael Llerena; Collins, Sebastián E.; Portela, Raquel; Bañares, Miguel Á.; Briand, Laura E.

doi:10.1016/j.mcat.2021.111811

Cited by 10 publications

(10 citation statements)

References 44 publications

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“…Although this issue is of broad interest, technical difficulties due to the interference of the solid support result in a few works available on this topic. [17][18][19] The method presented here has the advantage of being simple, straightforward, and applicable to other non-conventional media and enzyme preparations as well.…”

Section: Discussionmentioning

confidence: 99%

“…The effects of MeOH and EtOH on the structure and function of lipases is of great interest due to their use as acyl acceptors in enzymatic synthesis reactions, [8,[17][18][19] as MeOH is widely used in biodiesel production, although it is a competitive inhibitor of free CALB, [24,[31][32][33][34] and EtOH is of growing relevance in renewable process design. [35] Nonetheless, their effects on N-435 are still unclear and unexplored.…”

Section: Effects Of Short-chain Alcohols On Calbmentioning

confidence: 99%

“…Nonetheless, only a few seminal works investigated about the impact of solvents on the structure and activity of immobilized CALB. [ 17–19 ]…”

Section: Introductionmentioning

confidence: 99%

“…Nonetheless, only a few seminal works investigated about the impact of solvents on the structure and activity of immobilized CALB. [17][18][19] In this work, we analyze in detail the effects of short-chain alcohols (methanol -MeOH; ethanol -EtOH -and tert-butanol -tBuOH) of particular interest in biocatalysis because they can be used both as acyl acceptors and as a (co)-solvents in synthetic reactions such as the production of biodiesel. [17][18][19][20][21][22][23] Our results indicate that alcohols at high concentration inactivate N-435 through the formation of protein aggregates and by the enzyme release from the solid support.…”

mentioning

confidence: 99%

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Short‐chain alcohols inactivate an immobilized industrial lipase through two different mechanisms

Mangiagalli

Ami

Divitiis

et al. 2022

Biotechnology Journal

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Broadly used in biocatalysis as acyl acceptors or (co)‐solvents, short‐chain alcohols often cause irreversible loss of enzyme activity. Understanding the mechanisms of inactivation is a necessary step toward the optimization of biocatalytic reactions and the design of enzyme‐based sustainable processes. The functional and structural responses of an immobilized enzyme, Novozym 435 (N‐435), exposed to methanol, ethanol, and tert‐butanol, are explored in this work. N‐435 consists of Candida antarctica lipase B (CALB) adsorbed on polymethacrylate beads and finds application in a variety of processes involving the presence of short‐chain alcohols. The nature of the N‐435 material required the development of an ad hoc method of structural analysis, based on Fourier transform infrared microspectroscopy, which was complemented by catalytic activity assays and by morphological observation by transmission electron microscopy. The inactivation of N‐435 was found to be highly dependent on alcohol concentration and occurs through two different mechanisms. Short‐chain alcohols induce conformational changes leading to CALB aggregation, which is only partially prevented by immobilization. Moreover, alcohol modifies the texture of the solid support promoting the enzyme release. Overall, knowledge of the molecular mechanisms underlying N‐435 inactivation induced by short‐chain alcohols promises to overcome the limitations that usually occur during industrial processes.

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Section: Discussionmentioning

confidence: 99%

Section: Effects Of Short-chain Alcohols On Calbmentioning

confidence: 99%

“…Nonetheless, only a few seminal works investigated about the impact of solvents on the structure and activity of immobilized CALB. [ 17–19 ]…”

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Short‐chain alcohols inactivate an immobilized industrial lipase through two different mechanisms

Mangiagalli

Ami

Divitiis

et al. 2022

Biotechnology Journal

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“…When the molar ratio of ibuprofen to glycerol is 1:4, 99% monoglyceride can be produced by selective esterification. This is of great significance in prodrug synthesis and shows that lipase catalysis has excellent potential in the field of prodrug synthesis …”

Section: Application Of Calb In Different Fields Of the Pharmaceutica...mentioning

confidence: 99%

Application of Lipase B from Candida antarctica in the Pharmaceutical Industry

Wang,

Zhang,

et al. 2023

Ind. Eng. Chem. Res.

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The use of biocatalysts in pharmaceutical production is an important approach for the pharmaceutical industry to achieve green manufacturing. Compared to other lipases, Candida antarctica lipase B (CALB) possesses numerous excellent characteristics due to its unique structure. It exhibits relatively strong catalytic activity toward both water-insoluble and water-soluble substances. It shows high selectivity in hydrolysis and organic synthesis reactions. These properties are crucial for drug synthesis. However, current research shows that the use of CALB as a catalyst still faces challenges such as high cost, poor stability, and difficulty in large-scale production. Therefore, this paper mainly explores the advantages of CALB in the pharmaceutical industry and the challenges that still need to be overcome. It introduces the application progress of CALB in the pharmaceutical industry and finally provides a prospect for future research directions, hoping to provide appropriate references for related research.

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New Insights into the Effect of the Zeolites Framework Topology on the Esterification Reactions: A Comparative Study from Experiments and Theoretical Calculations

2022

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Catalytic and molecular insights of the esterification of ibuprofen and ketoprofen with glycerol

Cited by 10 publications

References 44 publications

Short‐chain alcohols inactivate an immobilized industrial lipase through two different mechanisms

Short‐chain alcohols inactivate an immobilized industrial lipase through two different mechanisms

Application of Lipase B from Candida antarctica in the Pharmaceutical Industry

New Insights into the Effect of the Zeolites Framework Topology on the Esterification Reactions: A Comparative Study from Experiments and Theoretical Calculations

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