Synthesis of a series of amino acid derived ionic liquids and tertiary amines: green chemistry metrics including microbial toxicity and preliminary biodegradation data analysis

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F16%3A10328779" target="_blank" >RIV/00216208:11160/16:10328779 - isvavai.cz</a>

Result on the web

<a href="http://pubs.rsc.org/en/content/articlehtml/2016/gc/c6gc00415f" target="_blank" >http://pubs.rsc.org/en/content/articlehtml/2016/gc/c6gc00415f</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/c6gc00415f" target="_blank" >10.1039/c6gc00415f</a>

Result language

angličtina

Original language name

Synthesis of a series of amino acid derived ionic liquids and tertiary amines: green chemistry metrics including microbial toxicity and preliminary biodegradation data analysis

Original language description

A series of L-phenylalanine ionic liquids (ILs), L-tyrosine ILs, tertiary amino analogues and proposed transformation products (PTPs) have been synthesised. Antimicrobial toxicity data, as part of the green chemistry metrics evaluation and to supplement preliminary biodegradation studies, was determined for ILs, tertiary amino analogues and PTPs. Good to very good overall yields (76 to 87%) for the synthesis of 6 ILs from L-phenylalanine were achieved. A C-2-symmetric IL was prepared from TMS-imidazole in a one-pot two-step method in excellent yield (91%). Synthesis of the L-tyrosine IL derivatives utilised a simple protection group strategy by using an extra equivalent of the bromoacetyl bromide reagent. Improvements in the synthesis of the alpha-bromoamide alkylating reagent from L-phenylalanine were achieved, directed by green chemistry metric analysis. A solvent switch from dichloromethane to THF is described, however the yield was 15% lower. Antimicrobial activity testing of L-phenylalanine ILs, L-tyrosine ILs, tertiary amino analogues and PTPs, against 8 bacteria and 12 fungi strains, showed that no compound had a high antimicrobial activity, apart from an L-proline analogue. In this exceptional case, the highest toxicity (IC95 = 125 and 250 mu M) was observed towards the two Gram positive strains Staphylococcus aureus and Staphylococcus epidermidis respectively. High antimicrobial activity was not found for the other bacteria or fungi strains screened. Preliminary analysis of biodegradation data (Closed Bottle Test, OECD 301D) is presented. The pyridinium IL derivative is the preferred green IL of the series based on synthesis, toxicity and biodegradation considerations. This work is a joint study with Kummere and co-workers and the PTPs were selected as target compounds based on concurrent biodegradation studies by the Kummerer group. For the comprehensive biodegradation and transformation product analysis see the accompanying paper.

Czech name

—

Czech description

—

Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

—

Project

<a href="/en/project/GA15-07332S" target="_blank" >GA15-07332S: Natural Lactones and Lactams: Towards Diverse Biological Activities through Purposeful Synthetic Manipulations</a><br>

Continuities

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

Publication year

2016

Confidentiality

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

Name of the periodical

Green Chemistry

ISSN

1463-9262

e-ISSN

—

Volume of the periodical

18

Issue of the periodical within the volume

16

Country of publishing house

GB - UNITED KINGDOM

Number of pages

19

Pages from-to

4374-4392

UT code for WoS article

000381440800006

EID of the result in the Scopus database

2-s2.0-84981524599