Enzymes-Catalyzed Knoevenagel Condensation Promoted by Ionic Liquid and Deep Eutectic Solvent

Wang, Yun; Cheng, Hong; He, Jia-Rui; Yao, Qiao-Xia; Li, Liling; Liang, Zhi-Hui; Li, Xiang

doi:10.1007/s10562-021-03718-1

Cited by 15 publications

(9 citation statements)

References 29 publications

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“…The use of hydrolases as catalysts in various variants of the Michael addition of different nucleophilic partners has been widely discussed in the literature [ 44 , 45 , 46 ]. Recently, it was also shown that lipases catalyze aldol and Knoevenagel condensations [ 47 ]. This observation prompted us to investigate the viability of β-phosphonomalononitriles synthesis using the Knoevenagel–phospha–Michael addition of alkyl phosphites to simultaneously generated α,β-unsaturated malonates in the presence of enzymes as an efficient and sustainable catalyst of both transformations.…”

Section: Resultsmentioning

confidence: 99%

Promiscuous Lipase-Catalyzed Knoevenagel–Phospha–Michael Reaction for the Synthesis of Antimicrobial β-Phosphono Malonates

Samsonowicz-Górski

Koszelewski

Kowalczyk

et al. 2022

IJMS

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An enzymatic route for phosphorous–carbon bond formation was developed by discovering new promiscuous activity of lipase. We reported a new metal-free biocatalytic method for the synthesis of pharmacologically relevant β-phosphonomalononitriles via a lipase-catalyzed one-pot Knoevenagel–phospha–Michael reaction. We carefully analyzed the best conditions for the given reaction: the type of enzyme, temperature, and type of solvent. A series of target compounds was synthesized, with yields ranging from 43% to 93% by enzymatic reaction with Candida cylindracea (CcL) lipase as recyclable and, a few times, reusable catalyst. The advantages of this protocol are excellent yields, mild reaction conditions, low costs, and sustainability. The applicability of the same catalyst in the synthesis of β-phosphononitriles is also described. Further, the obtained compounds were validated as new potential antimicrobial agents with characteristic E. coli bacterial strains. The pivotal role of such a group of phosphonate derivatives on inhibitory activity against selected pathogenic E. coli strains was revealed. The observed results are especially important in the case of the increasing resistance of bacteria to various drugs and antibiotics. The impact of the β-phosphono malonate chemical structure on antimicrobial activity was demonstrated. The crucial role of the substituents attached to the aromatic ring on the inhibitory action against selected pathogenic E. coli strains was revealed. Among tested compounds, four β-phosphonate derivatives showed an antimicrobial activity profile similar to that obtained with currently used antibiotics such as ciprofloxacin, bleomycin, and cloxacillin. In addition, the obtained compounds constitute a convenient platform for further chemical functionalization, allowing for a convenient change in their biological activity profile. It should also be noted that the cost of the compounds obtained is low, which may be an attractive alternative to the currently used antimicrobial agents. The observed results are especially important because of the increasing resistance of bacteria to various drugs and antibiotics.

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Section: Resultsmentioning

confidence: 99%

Promiscuous Lipase-Catalyzed Knoevenagel–Phospha–Michael Reaction for the Synthesis of Antimicrobial β-Phosphono Malonates

Samsonowicz-Górski

Koszelewski

Kowalczyk

et al. 2022

IJMS

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“…DESs have attracted the attention of the scientific community because of their potential applications. These mixtures can be used in organic synthesis, electrochemistry, extraction media [30][31][32][33][34], biotechnology or biodiesel [35][36][37] synthesis and separation processes [38,39], as a solvent in biological assays or enzymatic reactions [40], in biocatalysis [41,42], or in biomedical applications [43][44][45][46]. Additionally, they have been used in the pharmaceutical industry as excipients for increasing the solubility of hydrophobic drugs, or in drug delivery formulations [47][48][49][50][51].…”

Section: Deep Eutectic Solvents (Dess)mentioning

confidence: 99%

Deep Eutectic Solvents: Are They Safe?

et al. 2021

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Deep eutectic solvents (DESs) are a relatively new type of solvent that have attracted the attention of the scientific community due to their environmentally friendly properties and their versatility in many applications. Many possible DESs have been described and, thus, it is not easy to unequivocally characterize and generalize their properties. This is especially important in the case of the (eco)toxicity information that can be found for these mixtures. In this review, we collect data on the human and environmental toxicity of DESs, with the aim of gathering and exploring the behavioral patterns of DESs. The toxicity data found were analyzed attending to different factors: hydrogen bond donors or acceptors that form part of the eutectic mixture, pH, and the presence of organic acids in the DES molar ratio of the components, or interactions with natural compounds. In the case of ecotoxicity, results generally depend on the biomodel studied, along with other factors that have been also revised. Finally, we also carried out a revision of the biodegradation of DESs.

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“…1 H NMR spectra were recorded with a standard one-pulse sequence with 90 flip angles for excitation, a spectral width of 16 ppm centred at 5 ppm, 16 K data points and a relaxation time fixed to 30 s. Eight scans were acquired for the spectrum. In the case of 13 C, NMR spectra were recorded with an APT sequence (Bruker pulse program jmod), with a spectral width of 240 ppm centred at 110 ppm, 64 K data points and relaxation time fixed to 2 s. A total of 256 scans were acquired for each spectrum. COSY, HSQC and HMBC techniques with several Brucker pulse programs ( cosygpmfqf, hsqcedetgp and hmbclpndqf, respectively) were used for signal assignment.…”

Section: Nmr Measurementsmentioning

confidence: 99%

“…The chemical structure of ChCl:resorcinol (1:2), which was synthetized in this work, was analysed through NMR spectroscopy. The 1 H and 13 C spectra allowed the identification of the atoms present in the structure. These spectra are shown in Fig.…”

Section: Nmr Characterizationmentioning

confidence: 99%

Thermophysical characterization of choline chloride: Resorcinol and its mixtures with water

Lomba

Tucciarone

Ginera

et al. 2022

Fluid Phase Equilibria

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Enzymes-Catalyzed Knoevenagel Condensation Promoted by Ionic Liquid and Deep Eutectic Solvent

Cited by 15 publications

References 29 publications

Promiscuous Lipase-Catalyzed Knoevenagel–Phospha–Michael Reaction for the Synthesis of Antimicrobial β-Phosphono Malonates

Promiscuous Lipase-Catalyzed Knoevenagel–Phospha–Michael Reaction for the Synthesis of Antimicrobial β-Phosphono Malonates

Deep Eutectic Solvents: Are They Safe?

Thermophysical characterization of choline chloride: Resorcinol and its mixtures with water

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