Biocatalysis in Organic Solvents, Supercritical Fluids and Ionic Liquids

Cao, Chen; Matsuda, Tomoko

doi:10.1016/b978-0-12-411518-7.00003-2

Cited by 14 publications

(6 citation statements)

References 61 publications

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“…ity of hydrophobic substrates and the chemo-, regio-, and enantioselectivity of enzymes are often increased. [4][5][6][7] It has been reported that in some cases nonconventional media can impair enzyme activity and stability. [8][9][10] Enzyme inactivation can be irreversible, that is, due to protein denaturation and aggregation, or reversible, due to competition between the solvent and substrate molecules to bind the active site.…”

mentioning

confidence: 99%

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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mentioning

confidence: 99%

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

Mangiagalli

Ami

Divitiis

et al. 2022

Biotechnology Journal

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“…A non‐aqueous solvent is essential for lipase to catalyze the synthesis of esters. The solvent selected will not only affect the stability of the enzyme, but also the solubility in the substrate 29,30 . Based on the structural similarity of sucrose esters and VAA, six solvents previously reported for the synthesis of sucrose esters were screened 31,32 .…”

Section: Discussionmentioning

confidence: 99%

Synthesis of a series of validoxylamine A esters and their biological activities

Kang

Zhu

et al. 2021

Pest Management Science

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BACKGROUND The worldwide reduction in food production due to pests and diseases is still an important challenge facing today. Validoxylamine A (VAA) is a natural polyhydroxyl compound derived from validamycin, acting as an efficient trehalase inhibitor with insecticidal and antifungal activities. To extend the application and discover green pesticide, a series of ester derivatives were prepared based on VAA as a lead compound. Their biological activities were investigated against three typically agricultural disease, Rhizoctonia solani, Sclerotinia sclerotiorum and Aphis craccivora. RESULTS This study involved 30 novel validoxylamine A fatty acid esters (VAFAEs) synthesized by Novozym 435 and they were characterized with high‐resolution electrospray ionization mass spectrometry (HR‐ESI‐MS) and proton nuclear magnetic resonance (1H‐NMR). Of these 30 derivatives, most compounds showed improved antifungal activity, and 12 novel compounds showed improved insecticidal activity. When reacted with pentadecanoic acid, compound 14 showed the highest inhibitory activity against R. solani [median effective concentration (EC50) 0.01 μmol L−1], while the EC50 value of VAA was 34.99 μmol L−1. Furthermore, 21 novel VAFAEs showed higher inhibitory activity against S. sclerotiorum. Validoxylamine A oleic acid ester, compound 21, exhibited the highest insecticidal activity against A. craccivora [median lethal concentration (LC50) 39.63 μmol L−1], while the LC50 value of Pymetrozine was 50.45 μmol L−1, a commercialized pesticide against A. craccivora. CONCLUSION Combining our results, esterification of VAA by introducing different acyl donors was beneficial for the development of new eco‐friendly drugs in the field of pesticides.

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“…Biphasic systems could, at the same time, facilitate downstream processing. 54,55 Furthermore, due to addressed enzyme deactivation, immobilization methods should be investigated. This could hypothetically enable the biocatalytic reaction in continuous processes in biphasic systems.…”

Section: Challenges Regarding Industrial Implementation Of the Halohy...mentioning

confidence: 99%

Halohydrin dehalogenase-catalysed synthesis of enantiopure fluorinated building blocks: bottlenecks found and explained by applying a reaction engineering approach

et al. 2023

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Biocatalysis in Organic Solvents, Supercritical Fluids and Ionic Liquids

Cited by 14 publications

References 61 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

Synthesis of a series of validoxylamine A esters and their biological activities

Halohydrin dehalogenase-catalysed synthesis of enantiopure fluorinated building blocks: bottlenecks found and explained by applying a reaction engineering approach

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