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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

—

Projekt

<a href="/cs/project/GA15-07332S" target="_blank" >GA15-07332S: Přírodní laktony a laktamy: Účelné syntetické variace vedoucí k rozmanitým biologických aktivitám</a><br>

Návaznosti

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

Rok uplatnění

2016

Kód důvěrnosti údajů

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

Název periodika

Green Chemistry

ISSN

1463-9262

e-ISSN

—

Svazek periodika

18

Číslo periodika v rámci svazku

16

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

19

Strana od-do

4374-4392

Kód UT WoS článku

000381440800006

EID výsledku v databázi Scopus

2-s2.0-84981524599