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

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F23%3A10471777" target="_blank" >RIV/00216208:11160/23:10471777 - isvavai.cz</a>

Výsledek na webu

<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=LeVRSS5tcl" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=LeVRSS5tcl</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.molliq.2023.121285" target="_blank" >10.1016/j.molliq.2023.121285</a>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

A series of dipeptide ionic liquids (ILs) with L-phenylalanine and L-alanine fragments in structure were synthesized and their possible degradation pathways were analyzed. Based on this analysis, potential transformation products (PTPs) were proposed and synthesized. All of these compounds (25 in total) went through microbial toxicity screening and aerobic biodegradation testing. Obtained results demonstrated that by investigating ILs and PTPs with a dipeptide fragment (in tandem with single amino acid analogues), the design of ILs with high biodegradation values in closed bottle test can be accomplished. One finding was that within the scope of the compounds studied, L-phenylalanine containing compounds were more biodegradable than L-alanine derivatives. In addition to the choice of amino acid residue, its position in the dipeptide IL structure also had a significant effect on biodegradability. PyCH2CO-Phe-AlaOEt IL, where L-phenylalanine was in close proximity to the positively charged pyridinium sub-unit, gave higher biodegradation percentages compared to PyCH2CO-Ala-Phe-OEt IL, where alanine was closer to pyridinium than the phenylalanine residue. Analysis of PTPs data showed that the presence of an alanine residue resulted in undesirable (less green) PTPs more often compared to PTPs containing phenylalanine, especially when alanine was in close proximity to the pyridinium headgroup. Based on both toxicity and biodegradation testing results preferable and less preferable subunits can be chosen for the design of new sustainable chemicals based on amino acids. Results from this study demonstrate a potential of designing new sustainable chemicals using amino acid moieties as part of their structure.

Název v anglickém jazyce

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

Popis výsledku anglicky

A series of dipeptide ionic liquids (ILs) with L-phenylalanine and L-alanine fragments in structure were synthesized and their possible degradation pathways were analyzed. Based on this analysis, potential transformation products (PTPs) were proposed and synthesized. All of these compounds (25 in total) went through microbial toxicity screening and aerobic biodegradation testing. Obtained results demonstrated that by investigating ILs and PTPs with a dipeptide fragment (in tandem with single amino acid analogues), the design of ILs with high biodegradation values in closed bottle test can be accomplished. One finding was that within the scope of the compounds studied, L-phenylalanine containing compounds were more biodegradable than L-alanine derivatives. In addition to the choice of amino acid residue, its position in the dipeptide IL structure also had a significant effect on biodegradability. PyCH2CO-Phe-AlaOEt IL, where L-phenylalanine was in close proximity to the positively charged pyridinium sub-unit, gave higher biodegradation percentages compared to PyCH2CO-Ala-Phe-OEt IL, where alanine was closer to pyridinium than the phenylalanine residue. Analysis of PTPs data showed that the presence of an alanine residue resulted in undesirable (less green) PTPs more often compared to PTPs containing phenylalanine, especially when alanine was in close proximity to the pyridinium headgroup. Based on both toxicity and biodegradation testing results preferable and less preferable subunits can be chosen for the design of new sustainable chemicals based on amino acids. Results from this study demonstrate a potential of designing new sustainable chemicals using amino acid moieties as part of their structure.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

<a href="/cs/project/GA22-19209S" target="_blank" >GA22-19209S: Heterodendralenový přístup k syntéze isokumarinů a isolykoricidinů</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2023

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Molecular Liquids

ISSN

0167-7322

e-ISSN

1873-3166

Svazek periodika

374

Číslo periodika v rámci svazku

March

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

13

Strana od-do

121285

Kód UT WoS článku

000925859700001

EID výsledku v databázi Scopus

2-s2.0-85146595796