Keratin Protein-Catalyzed Nitroaldol (Henry) Reaction and Comparison with Other Biopolymers

Häring, Marleen; Pettignano, Asja; Quignard, Françoise; Tanchoux, Nathalie; Díaz, David Díaz

doi:10.3390/molecules21091122

Cited by 12 publications

(4 citation statements)

References 22 publications

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“…Our group and others have demonstrated that the nitroaldol (Henry) reaction can be mediated by different biopolymers and enzymes . In the case of Au@apoferritin scaffolds, the potential catalytic activity could in principle arise from exposed basic groups of the protein itself and/or Au nanoparticles confined inside the apoferritin cage acting as a nanoreactor .…”

Section: Resultsmentioning

confidence: 99%

Catalytic Macroporous Biohydrogels Made of Ferritin‐Encapsulated Gold Nanoparticles

et al. 2016

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Reported is a modular approach for the incorporation and stabilization of gold nanoparticles inside a three‐dimensional macroporous hydrogel made of ferritin. The strategy, which involves the dynamic templating of surfactant H1 domains, demineralization, and remineralization helps to overcome aggregation and degradation issues usually associated with bare‐metal‐based nanocatalysts. The catalytic activity of the so‐synthesized bionanocomposite hydrogel was demonstrated in both nitroaldol (Henry) and nitroreduction model reactions in aqueous solution at room temperature. An interesting synergistic effect between basic residues of the protein and the gold nanoparticles was found in the nitroaldol reaction when carried out in water in the presence of a phase‐transfer catalyst. Furthermore, the reduction of 4‐nitrophenol and 4‐nitroaniline catalyzed by the nanocomposite scaffold in the presence of NaBH4 proceeded significantly faster than that using other known Au‐ and Ag‐based catalysts under similar conditions.

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Section: Resultsmentioning

confidence: 99%

Catalytic Macroporous Biohydrogels Made of Ferritin‐Encapsulated Gold Nanoparticles

et al. 2016

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“…Wood ash biocatalyst [63], alginic acid [64,65], boric acid [66], tartaric acid [67,68], citric acid [69][70][71], pectin [72], oxalic acid [73][74][75], saccharin [46,76,77], wool and keratin deriving from wool fibers [78][79][80], feathers [81][82][83][84], silk [85,86], plant derivatives, lemon juice [87,88].…”

Section: Natural Materials and Foods As Catalystsmentioning

confidence: 99%

Green Chemistry in Organic Synthesis: Recent Update on Green Catalytic Approaches in Synthesis of 1,2,4-Thiadiazoles

et al. 2022

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Green (sustainable) chemistry provides a framework for chemists, pharmacists, medicinal chemists and chemical engineers to design processes, protocols and synthetic methodologies to make their contribution to the broad spectrum of global sustainability. Green synthetic conditions, especially catalysis, are the pillar of green chemistry. Green chemistry principles help synthetic chemists overcome the problems of conventional synthesis, such as slow reaction rates, unhealthy solvents and catalysts and the long duration of reaction completion time, and envision solutions by developing environmentally benign catalysts, green solvents, use of microwave and ultrasonic radiations, solvent-free, grinding and chemo-mechanical approaches. 1,2,4-thiadiazole is a privileged structural motif that belongs to the class of nitrogen–sulfur-containing heterocycles with diverse medicinal and pharmaceutical applications. This comprehensive review systemizes types of green solvents, green catalysts, ideal green organic synthesis characteristics and the green synthetic approaches, such as microwave irradiation, ultrasound, ionic liquids, solvent-free, metal-free conditions, green solvents and heterogeneous catalysis to construct different 1,2,4-thiadiazoles scaffolds.

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“…In a very detailed review [ 21 ], the first thing that catches the eye is that wool powder proved not only to be a valuable tool for catalysis itself, as a specific source of keratin, but also a complexing agent for metal compounds of relevance in catalysis. Offering some examples, we introduce an innovative work released in 2016 [ 22 ], which confers to wool powder the role of support for nitroaldol reactions. The idea is quite simple: keratin deriving from wool fibers (unfortunately no detailed treatments are reported), in the presence of a mixture of H 2 O/TBAB, can afford nitroaldol products in high yields ( Scheme 1 ), perfectly stackable with results obtained with other polymers and comparable with other previous experiments, which involve the use of DMSO as a solvent.…”

Section: Woolmentioning

confidence: 99%

“…Metals have contributed predominantly in the context of C-C bond formation [ 23 , 24 , 25 ] Hydrogenations and hydrations have also been thoroughly studied, [ 26 , 27 ] so intensively that it would be impossible to report them all in this review. Still, on this topic, the review mentioned above [ 22 ] comes to our rescue, proposing us a series of examples reported in the literature about new wool-mediated approaches. Due to the high content of cysteine, these fibres can efficiently complex transition metals, especially palladium.…”

Section: Woolmentioning

confidence: 99%

Appealing Renewable Materials in Green Chemistry

et al. 2022

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In just a few years, chemists have significantly changed their approach to the synthesis of organic molecules in the laboratory and industry. Researchers are encouraged to approach “greener” reagents, solvents, and methodologies, to go hand in hand with the world’s environmental matter, such as water, soil, and air pollution. The employment of plant and animal derivates that are commonly regarded as “waste material” has paved the way for the development of new green strategies. In this review, the most important innovations in this field have been highlighted, paying due attention to those materials that have played a crucial role in organic reactions: wool, silk, and feather. Moreover, we decided to focus on the other most important supports and catalysts in green syntheses, such as proteins and their derivates. Different materials have shown prominent activity in the adsorption of metals and organic dyes, which has constituted a relevant scope in the last two decades. We intend to furnish a complete screening of the application given to these materials and contribute to their potential future utilization.

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Keratin Protein-Catalyzed Nitroaldol (Henry) Reaction and Comparison with Other Biopolymers

Cited by 12 publications

References 22 publications

Catalytic Macroporous Biohydrogels Made of Ferritin‐Encapsulated Gold Nanoparticles

Catalytic Macroporous Biohydrogels Made of Ferritin‐Encapsulated Gold Nanoparticles

Green Chemistry in Organic Synthesis: Recent Update on Green Catalytic Approaches in Synthesis of 1,2,4-Thiadiazoles

Appealing Renewable Materials in Green Chemistry

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