Co-immobilization of metal and enzyme into hydrophobic nanopores for highly improved chemoenzymatic asymmetric synthesis

Gao, Liya; Wang, Zihan; Liu, Yunting; Liu, Pengbo; Gao, Shiqi; Gao, Jing; Jiang, Yanjun

doi:10.1039/d0cc06431a

Cited by 27 publications

(18 citation statements)

References 37 publications

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“…According to our previously reported method, [ 31 ] the hydrophobic DON‐based metal (DON@Pd) and enzyme (DON@ADH) catalysts were firstly synthesized by immobilizing Pd nanoparticles (Pd NPs) and alcohol dehydrogenase (ADH, from Rhodococcus ruber ) on the wrinkles of DONs, respectively. Mussel‐inspired PDA with functional catechol hydroxyl and amine groups was selected as hydrophilic shell to fabricate amphiphilic catalysts due to its biocompatibility, permeability and self‐adhesive capability.…”

Section: Resultsmentioning

confidence: 99%

“…Recently, our group synthesized a metal‐enzyme integrated catalyst by co‐immobilization of MNPs and enzymes on dendritic organosilica nanoparticles (DONs), which exhibited high catalytic activity in chemoenzymatic asymmetric synthesis in organic solvent and biphasic system. [ 31 ] However, the catalytic performance of the DON‐based catalysts in water has not been investigated. As a part of our continued interest in fabricating metal/enzyme heterogeneous catalysts for green and efficient organic reactions, [ 32‐35 ] we herein coated the DON‐based catalysts with hydrophilic polydopamine (PDA) shell to fabricate amphiphilic catalysts for highly efficient heterogeneous catalysis in water, including Pd‐catalyzed cross‐couplings and enzymatic enantioselective reduction.…”

Section: Background and Originality Contentmentioning

confidence: 99%

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Polydopamine‐Encapsulated Dendritic Organosilica Nanoparticles as Amphiphilic Platforms for Highly Efficient Heterogeneous Catalysis in Water

et al. 2021

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Main observation and conclusion Aqueous heterogeneous catalysis is a green, sustainable catalytic process that attracts increasing attention, but it often suffers from poor mass transfer, substrate adsorption and catalyst dispersion. Herein, we synthesized a type of amphiphilic core‐shell catalysts with a hydrophilic polydopamine (PDA) shell and a hydrophobic dendritic organosilica nanoparticle (DON) core for heterogeneous catalysis in water. The hydrophilic shell allowed the catalyst dispersing well in water, and the hydrophobic core facilitated the absorption of organic reactants. The hierarchical core‐shell structure facilitated rational arrangement of the location of catalytic species to match the reaction sequence. The obtained metal, enzyme and metal‐enzyme amphiphilic catalysts demonstrated improved stability, selectivity and activity in aqueous reactions, including Pd‐catalyzed cross‐couplings (Suzuki, Liebeskind‐Srogl, Heck and Sonogashira), enzymatic enantioselective reduction, chemoenzymatic cascade synthesis of chiral compounds and chemoenzymatic cascade degradation of organophosphates. The amphiphilic catalysts could be easily in situ recovered, and their high catalytic performance was sustained for five cycles.

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Section: Resultsmentioning

confidence: 99%

Section: Background and Originality Contentmentioning

confidence: 99%

Polydopamine‐Encapsulated Dendritic Organosilica Nanoparticles as Amphiphilic Platforms for Highly Efficient Heterogeneous Catalysis in Water

et al. 2021

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“…Siliceous mesocellular foam CAL-B/Pd DKR of amines [169]; ketone reduction/KR cascade [170,171] Laccase/Pd Oxidation of alcohols [172] and 2-substituted-2,3-dihydroquinazolin-4(1H)-ones [173] Silica nanoparticles CAL-B/Pd DKR of amines [174,175]; aldehyde reduction/alcohol esterification cascade [176] Silica-coated iron oxide nanoparticles CAL-B/Pd DKR of amines [177] Dendritic organosilica nanoparticles CAL-B/Pd DKR of amines [178] Pd/ADH Pd/Cu-catalyzed Liebeskind-Strogl reaction/bioreduction cascade [178] HKUST-1 (MOF) Cu/ADH Benzaldehyde oxidation [183] NaDC/Mi MBN Shvö's catalyst/CAL-B DKR of alcohols and amines [184] Carbon nitride (C 3 N 4 ) Pd/CAL-B aldehyde reduction/alcohol esterification cascade [185] There are fewer reports of co-immobilization of enzymes and chemocatalysts to date when compared to co-immobilization of enzymes solely. Although most enzymes are compatible with each other and operate under similar conditions, mutual inactivation and different, divergent operational conditions are often a crucial issue in the development of chemo-bio hybrid catalysts.…”

Section: Matrix Biocatalyst/chemocatalyst Applicationsmentioning

confidence: 99%

“…Dendritic organosilica nanoparticles (DONs) are hydrophobic materials with ordered center-radial mesoporous channels presenting internal surface areas that can be easily accessed. The use of DONs to co-immobilize Pd and lipase CAL-B has been recently reported [178]. In this work, Pd was immobilized in DONs through in situ reduction, which was followed by immobilization of lipase through physical adsorption.…”

Section: Co-immobilization Of Enzymes and Metals In Siliceous Materialsmentioning

confidence: 99%

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Multicatalytic Hybrid Materials for Biocatalytic and Chemoenzymatic Cascades—Strategies for Multicatalyst (Enzyme) Co-Immobilization

et al. 2021

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During recent decades, the use of enzymes or chemoenzymatic cascades for organic chemistry has gained much importance in fundamental and industrial research. Moreover, several enzymatic and chemoenzymatic reactions have also served in green and sustainable manufacturing processes especially in fine chemicals, pharmaceutical, and flavor/fragrance industries. Unfortunately, only a few processes have been applied at industrial scale because of the low stabilities of enzymes along with the problematic processes of their recovery and reuse. Immobilization and co-immobilization offer an ideal solution to these problems. This review gives an overview of all the pathways for enzyme immobilization and their use in integrated enzymatic and chemoenzymatic processes in cascade or in a one-pot concomitant execution. We place emphasis on the factors that must be considered to understand the process of immobilization. A better understanding of this fundamental process is an essential tool not only in the choice of the best route of immobilization but also in the understanding of their catalytic activity.

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Molecular Engineering and Morphology Control of Covalent Organic Frameworks for Enhancing Activity of Metal‐Enzyme Cascade Catalysis

Zhao,

Zhang,

Liu

et al. 2024

Advanced Science

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Metal‐enzyme integrated catalysts (MEICs) that combine metal and enzyme offer great potential for sustainable chemoenzymatic cascade catalysis. However, rational design and construction of optimal microenvironments and accessible active sites for metal and enzyme in individual nanostructures are necessary but still challenging. Herein, Pd nanoparticles (NPs) and Candida antarctica lipase B (CALB) are co‐immobilized into the pores and surfaces of covalent organic frameworks (COFs) with tunable functional groups, affording Pd/COF‐X/CALB (X = ONa, OH, OMe) MEICs. This strategy can regulate the microenvironment around Pd NPs and CALB, and their interactions with substrates. As a result, the activity of the COF‐based MEICs in catalyzing dynamic kinetic resolution of primary amines is enhanced and followed COF‐OMe > COF‐OH > COF‐ONa. The experimental and simulation results demonstrated that functional groups of COFs modulated the conformation of CALB, the electronic states of Pd NPs, and the affinity of the integrated catalysts to the substrate, which contributed to the improvement of the catalytic activity of MEICs. Further, the MEICs are prepared using COF with hollow structure as support material, which increased accessible active sites and mass transfer efficiency, thus improving catalytic performance. This work provides a blueprint for rational design and preparation of highly active MEICs.

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Co-immobilization of metal and enzyme into hydrophobic nanopores for highly improved chemoenzymatic asymmetric synthesis

Abstract: A facile, general strategy to fabricate metal–enzyme catalysts with hydrophobic microenvironment for highly improved chemoenzymatic asymmetric synthesis.

Cited by 27 publications

References 37 publications

Polydopamine‐Encapsulated Dendritic Organosilica Nanoparticles as Amphiphilic Platforms for Highly Efficient Heterogeneous Catalysis in Water

Polydopamine‐Encapsulated Dendritic Organosilica Nanoparticles as Amphiphilic Platforms for Highly Efficient Heterogeneous Catalysis in Water

Multicatalytic Hybrid Materials for Biocatalytic and Chemoenzymatic Cascades—Strategies for Multicatalyst (Enzyme) Co-Immobilization

Molecular Engineering and Morphology Control of Covalent Organic Frameworks for Enhancing Activity of Metal‐Enzyme Cascade Catalysis

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