Heterocycles 36. Single-Walled Carbon Nanotubes-Bound N,N-Diethyl Ethanolamine as Mild and Efficient Racemisation Agent in the Enzymatic DKR of 2-Arylthiazol-4-yl-alanines

In this paper we describe the chemoenzymatic synthesis of enantiopure l-2-arylthiazol-4-yl alanines starting from their racemic N-acetyl derivatives; by combining the lipase-catalysed dynamic kinetic resolution of oxazol-5(4H)-ones with a chemical and an enzymatic enantioselective hydrolytic step af...

Descripción completa

Detalles Bibliográficos
Autores principales: Leonte, Denisa, Bencze, László Csaba, Paizs, Csaba, Toşa, Monica Ioana, Zaharia, Valentin, Irimie, Florin Dan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273000/
https://www.ncbi.nlm.nih.gov/pubmed/26712727
http://dx.doi.org/10.3390/molecules21010025
_version_ 1783377283669557248
author Leonte, Denisa
Bencze, László Csaba
Paizs, Csaba
Toşa, Monica Ioana
Zaharia, Valentin
Irimie, Florin Dan
author_facet Leonte, Denisa
Bencze, László Csaba
Paizs, Csaba
Toşa, Monica Ioana
Zaharia, Valentin
Irimie, Florin Dan
author_sort Leonte, Denisa
collection PubMed
description In this paper we describe the chemoenzymatic synthesis of enantiopure l-2-arylthiazol-4-yl alanines starting from their racemic N-acetyl derivatives; by combining the lipase-catalysed dynamic kinetic resolution of oxazol-5(4H)-ones with a chemical and an enzymatic enantioselective hydrolytic step affording the desired products in good yields (74%–78%) and high enantiopurities (ee > 99%). The developed procedure exploits the utility of the single-walled carbon nanotubes-bound diethylaminoethanol as mild and efficient racemisation agent for the dynamic kinetic resolution of the corresponding oxazolones.
format Online
Article
Text
id pubmed-6273000
institution National Center for Biotechnology Information
language English
publishDate 2015
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-62730002018-12-28 Heterocycles 36. Single-Walled Carbon Nanotubes-Bound N,N-Diethyl Ethanolamine as Mild and Efficient Racemisation Agent in the Enzymatic DKR of 2-Arylthiazol-4-yl-alanines Leonte, Denisa Bencze, László Csaba Paizs, Csaba Toşa, Monica Ioana Zaharia, Valentin Irimie, Florin Dan Molecules Article In this paper we describe the chemoenzymatic synthesis of enantiopure l-2-arylthiazol-4-yl alanines starting from their racemic N-acetyl derivatives; by combining the lipase-catalysed dynamic kinetic resolution of oxazol-5(4H)-ones with a chemical and an enzymatic enantioselective hydrolytic step affording the desired products in good yields (74%–78%) and high enantiopurities (ee > 99%). The developed procedure exploits the utility of the single-walled carbon nanotubes-bound diethylaminoethanol as mild and efficient racemisation agent for the dynamic kinetic resolution of the corresponding oxazolones. MDPI 2015-12-25 /pmc/articles/PMC6273000/ /pubmed/26712727 http://dx.doi.org/10.3390/molecules21010025 Text en © 2015 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons by Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Leonte, Denisa
Bencze, László Csaba
Paizs, Csaba
Toşa, Monica Ioana
Zaharia, Valentin
Irimie, Florin Dan
Heterocycles 36. Single-Walled Carbon Nanotubes-Bound N,N-Diethyl Ethanolamine as Mild and Efficient Racemisation Agent in the Enzymatic DKR of 2-Arylthiazol-4-yl-alanines
title Heterocycles 36. Single-Walled Carbon Nanotubes-Bound N,N-Diethyl Ethanolamine as Mild and Efficient Racemisation Agent in the Enzymatic DKR of 2-Arylthiazol-4-yl-alanines
title_full Heterocycles 36. Single-Walled Carbon Nanotubes-Bound N,N-Diethyl Ethanolamine as Mild and Efficient Racemisation Agent in the Enzymatic DKR of 2-Arylthiazol-4-yl-alanines
title_fullStr Heterocycles 36. Single-Walled Carbon Nanotubes-Bound N,N-Diethyl Ethanolamine as Mild and Efficient Racemisation Agent in the Enzymatic DKR of 2-Arylthiazol-4-yl-alanines
title_full_unstemmed Heterocycles 36. Single-Walled Carbon Nanotubes-Bound N,N-Diethyl Ethanolamine as Mild and Efficient Racemisation Agent in the Enzymatic DKR of 2-Arylthiazol-4-yl-alanines
title_short Heterocycles 36. Single-Walled Carbon Nanotubes-Bound N,N-Diethyl Ethanolamine as Mild and Efficient Racemisation Agent in the Enzymatic DKR of 2-Arylthiazol-4-yl-alanines
title_sort heterocycles 36. single-walled carbon nanotubes-bound n,n-diethyl ethanolamine as mild and efficient racemisation agent in the enzymatic dkr of 2-arylthiazol-4-yl-alanines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273000/
https://www.ncbi.nlm.nih.gov/pubmed/26712727
http://dx.doi.org/10.3390/molecules21010025
work_keys_str_mv AT leontedenisa heterocycles36singlewalledcarbonnanotubesboundnndiethylethanolamineasmildandefficientracemisationagentintheenzymaticdkrof2arylthiazol4ylalanines
AT benczelaszlocsaba heterocycles36singlewalledcarbonnanotubesboundnndiethylethanolamineasmildandefficientracemisationagentintheenzymaticdkrof2arylthiazol4ylalanines
AT paizscsaba heterocycles36singlewalledcarbonnanotubesboundnndiethylethanolamineasmildandefficientracemisationagentintheenzymaticdkrof2arylthiazol4ylalanines
AT tosamonicaioana heterocycles36singlewalledcarbonnanotubesboundnndiethylethanolamineasmildandefficientracemisationagentintheenzymaticdkrof2arylthiazol4ylalanines
AT zahariavalentin heterocycles36singlewalledcarbonnanotubesboundnndiethylethanolamineasmildandefficientracemisationagentintheenzymaticdkrof2arylthiazol4ylalanines
AT irimieflorindan heterocycles36singlewalledcarbonnanotubesboundnndiethylethanolamineasmildandefficientracemisationagentintheenzymaticdkrof2arylthiazol4ylalanines

Ejemplares similares