Thermo-switchable hydrophobic deep eutectic solvent for CuAAC

Pouget, Florence Charnay; Andanson, Jean-Michel; Gautier, Arnaud

doi:10.1039/d3su00249g

RSC Sustain.

2023

DOI: 10.1039/d3su00249g

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Thermo-switchable hydrophobic deep eutectic solvent for CuAAC

Florence Charnay Pouget,

Jean-Michel Andanson,

Arnaud Gautier

Abstract: The copper alkyne–azide cycloaddition in a deep eutectic solvent possessing thermomorphic properties is reported. The system allows a facile separation of the hydrophilic product from the reagents and catalyst with a small thermal trigger.

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2024

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Cited by 2 publications

References 37 publications

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Redox Biocatalysis in Lidocaine‐Based Hydrophobic Deep Eutectic Solvents: Non‐Conventional Media Outperform Aqueous Conditions

Zhang,

Lahmann,

Bittner

et al. 2024

ChemSusChem

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Redox biocatalysis is an important pillar of the chemical industry. Yet, the enzymes’ nature restricts most reactions to aqueous conditions, where the limited substrate solubility leads to unsustainable diluted biotranformations. Non‐aqueous media represent a strategic solution to conduct intensified biocatalytic routes. Deep eutectic solvents (DESs) are designable solvents that can be customized to meet specific application needs. Within the large design space of combining DES components (and ratios), hydrophobic DESs hold the potential to be both enzyme‐compatible – keeping the enzymes’ hydration –, and solubilizers for hydrophobic reactants. We explored two hydrophobic DESs, lidocaine/oleic acid, and lidocaine/decanoic acid, as reaction media for carbonyl reduction catalyzed by horse liver alcohol dehydrogenase, focusing on the effect of water contents and on maximizing substrate loadings. Enzymes remained highly active and stable in the DESs with 20 wt.% buffer, whereas the reaction performance in DESs outperformed the pure buffer system with hydrophobic substrates (e.g., cinnamaldehyde to form the industrially relevant cinnamyl alcohol), with a 2‐fold higher specific activity. Notably, the cinnamaldehyde reduction was for the first time performed at 800 mM (~100 g[[EQUATION]]L‐1) with full conversion, which opens up new avenues to industrial applications of hydrophobic DESs for enzyme catalysis.

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Redox Biocatalysis in Lidocaine‐Based Hydrophobic Deep Eutectic Solvents: Non‐Conventional Media Outperform Aqueous Conditions

Zhang,

Lahmann,

Bittner

et al. 2024

ChemSusChem

View full text Add to dashboard Cite

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Selective Carbohydrate Deacetylation: Simple and Mild Approach based on Supported Copper Nanoparticles

Marchán‐García,

Lo Fiego,

Moglie

2024

Helvetica Chimica Acta

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Herein, a selective protocol for the complete removal of acetyl protecting groups from carbohydrate derivatives based on copper nanoparticles supported on activated carbon is presented. The deacetylation procedure occurs under neutral conditions, is applicable to a wide range of substrates and tolerates a variety of functional groups (e.g. azido, allyl and silyl groups). Quantitative yields of the deacetylated product were obtained for all evaluated derivatives using catalyst amounts between 1 and 10 mol%. As a special highlight, the dual behavior of the nanocatalyst in both deacetylation and click reactions is reported.

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Thermo-switchable hydrophobic deep eutectic solvent for CuAAC

Abstract: The copper alkyne–azide cycloaddition in a deep eutectic solvent possessing thermomorphic properties is reported. The system allows a facile separation of the hydrophilic product from the reagents and catalyst with a small thermal trigger.

Cited by 2 publications

References 37 publications

Redox Biocatalysis in Lidocaine‐Based Hydrophobic Deep Eutectic Solvents: Non‐Conventional Media Outperform Aqueous Conditions

Redox Biocatalysis in Lidocaine‐Based Hydrophobic Deep Eutectic Solvents: Non‐Conventional Media Outperform Aqueous Conditions

Selective Carbohydrate Deacetylation: Simple and Mild Approach based on Supported Copper Nanoparticles

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