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

Result code in 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>

Result on the web

<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>

Result language

angličtina

Original language name

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

Original language description

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.

Czech name

—

Czech description

—

Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

10403 - Physical chemistry

Project

<a href="/en/project/GA22-19209S" target="_blank" >GA22-19209S: Heterodendralene-based approach to isocoumarins and isolycoricidine</a><br>

Continuities

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

Publication year

2023

Confidentiality

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

Name of the periodical

Journal of Molecular Liquids

ISSN

0167-7322

e-ISSN

1873-3166

Volume of the periodical

374

Issue of the periodical within the volume

March

Country of publishing house

NL - THE KINGDOM OF THE NETHERLANDS

Number of pages

13

Pages from-to

121285

UT code for WoS article

000925859700001

EID of the result in the Scopus database

2-s2.0-85146595796