Design of sustainable ionic liquids based on l-phenylalanine and l-alanine dipeptides: Synthesis, toxicity and biodegradation studies

Капитанов, И. В.; Raba, Grete; Špulák, Marcel; Vilu, Raivo; Karpichev, Yevgen; Gathergood, Nicholas

doi:10.1016/j.molliq.2023.121285

Cited by 7 publications

(8 citation statements)

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“…Among the SAILs PyPheOC n and PyPheNHC n , which were the focus of our current study, there are several examples of compounds (with n = 4–8) that could be considered as low toxicity and readily biodegradable ILs [ 7 ]. An evaluation of the toxicity and biodegradability of potential hydrolytic decomposition products of PyPheOC n and PyPheNHC n , performed in our recent studies [ 10 , 24 , 32 ], also confirm a great potential of these SAILs as a platform for ecologically friendly sustainable systems. The solubilization capacity of PyPheOC n surfactants, evaluated related to model representative PAH (naphthalene, anthracene and pyrene), is comparable to the solubilization capacity of conventional cationic surfactant CTABr (see Table 1 and Figure 3 ; compare parameters for CTAB and SAILs with n = 8–12), but in the cases of PyPheOC n and PyPheNHC n , polycyclic aromatic hydrocarbons could be easily separated from the SAILs water solution using enzymatic decomposition of SAILs under mild conditions.…”

Section: Resultssupporting

confidence: 58%

“…The intermediates and final products of enzymatic decomposition were not dependent on the degradation pathway (A or B) and were readily biodegradable compounds [ 24 ], which is critically important for the design of sustainable ecologically friendly systems.…”

Section: Resultsmentioning

confidence: 99%

“…Synthesis of SAILs PyPheOC n is previously described [ 32 ]. Synthesis of PyPheNC 4 was performed according to common synthetic procedures [ 10 , 24 ], confirmation of the structure and purity was performed using 1 H, 13 C, 1 H- 1 H, 1 H- 13 C, DETP 135 NMR techniques and by HRMS.…”

Section: Methodsmentioning

confidence: 99%

“…The synthesis and investigation of ILs using natural structural elements is a prospective approach in designing new molecules [ 7 , 20 , 21 , 22 , 23 , 24 ]. The ILs based on the amino acids are considered as one of the green alternatives and have high demand in industrial applications, which lead to the further development of a benign by design approach for the elaboration of an L-phenylalanine ethyl ester platform for designing completely mineralizable ILs [ 23 , 25 ].…”

Section: Introductionmentioning

confidence: 99%

“…The imidazolium- and pyridinium-derived phenylalanine ethyl ester ILs were shown to be more biodegradable than the proline and choline derivatives [ 23 ]. Recent studies provided an insight into the biodegradability of the ethyl ester of cationic phenylanine-derived ILs [ 24 ]. The pyridinium derivatives are found to be the preferred greener IL based on synthesis, toxicity, and biodegradation considerations [ 7 ].…”

Section: Introductionmentioning

confidence: 99%

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Sustainable Phenylalanine-Derived SAILs for Solubilization of Polycyclic Aromatic Hydrocarbons

et al. 2023

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The solubilization capacity of a series of sustainable phenylalanine-derived surface-active ionic liquids (SAILs) was evaluated towards polycyclic aromatic hydrocarbons—naphthalene, anthracene and pyrene. The key physico-chemical parameters of the studied systems (critical micelle concentration, spectral properties, solubilization parameters) were determined, analyzed and compared with conventional cationic surfactant, CTABr. For all studied PAH solubilization capacity increases with extension of alkyl chain length of PyPheOCn SAILs reaching the values comparable to CTABr for SAILs with n = 10–12. A remarkable advantage of the phenylalanine-derived SAILs PyPheOCn and PyPheNHCn is a possibility to cleave enzymatically ester and/or amide bonds under mild conditions, to separate polycyclic aromatic hydrocarbons in situ. A series of immobilized enzymes was tested to determine the most suitable candidates for tunable decomposition of SAILs. The decomposition pathway could be adjusted depending on the choice of the enzyme system, reaction conditions, and selection of SAILs type. The evaluated systems can provide selective cleavage of the ester and amide bond and help to choose the optimal decomposition method of SAILs for enzymatic recycling of SAILs transformation products or as a pretreatment towards biological mineralization. The concept of a possible practical application of studied systems for PAHs solubilization/separation was also discussed focusing on sustainability and a green chemistry approach.

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Section: Resultssupporting

confidence: 58%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Sustainable Phenylalanine-Derived SAILs for Solubilization of Polycyclic Aromatic Hydrocarbons

et al. 2023

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Unexpected Energy Applications of Ionic Liquids

Matuszek,

Piper,

Brzęczek‐Szafran

et al. 2024

Advanced Materials

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Ionic liquids and their various analogues are without doubt the scientific sensation of the last few decades, paving the yellow brick road to a worldly version of Oz's green “Emerald city” – a more sustainable society. Their versatile suite of properties, originating from an almost inconceivably large number of possible cation and anion combinations, allows tuning of the structure to serve a desired purpose. Ionic liquids hence offer a myriad of useful applications from solvents to catalysts, through to lubricants, gas absorbers and azeotrope breakers. The purpose of this review is to explore the more unexpected of these applications, particularly in the energy space. It guides the reader through the application of ionic liquids and their analogues as i) phase change materials (PCMs) for thermal energy storage, ii) organic ionic plastic crystals (OIPCs), which have been studied as battery electrolytes and in gas separation, iii) key components in the nitrogen reduction reaction (NRR) for sustainable ammonia generation, iv) as electrolytes in aluminum ion batteries, and v) in other emerging technologies. We conclude that there is tremendous scope for further optimizing and tuning of the ionic liquid in its task, subject to sustainability imperatives in line with current global priorities, assisted by artificial intelligence.This article is protected by copyright. All rights reserved

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Sustainable ionic liquids-based molecular platforms for designing acetylcholinesterase reactivators

Kapitanov,

Špulák,

Pour

et al. 2023

Chemico-Biological Interactions

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Design of sustainable ionic liquids based on l-phenylalanine and l-alanine dipeptides: Synthesis, toxicity and biodegradation studies

Cited by 7 publications

References 58 publications

Sustainable Phenylalanine-Derived SAILs for Solubilization of Polycyclic Aromatic Hydrocarbons

Sustainable Phenylalanine-Derived SAILs for Solubilization of Polycyclic Aromatic Hydrocarbons

Unexpected Energy Applications of Ionic Liquids

Sustainable ionic liquids-based molecular platforms for designing acetylcholinesterase reactivators

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