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A Dimeric Thiourea CSA for the Enantiodiscrimination of Amino Acid Derivatives by NMR Spectroscopy
[Image: see text] The reaction of benzoyl isothiocyanate with (1R,2R)-1,2-bis(2-hydroxyphenyl)ethylenediamine afforded a new thiourea chiral solvating agent (CSA) with a very high ability to differentiate (1)H and (13)C NMR signals of simple amino acid derivatives, even at low concentrations. The en...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2021
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8279476/ https://www.ncbi.nlm.nih.gov/pubmed/34019407 http://dx.doi.org/10.1021/acs.joc.1c00340 |
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author | Recchimurzo, Alessandra Micheletti, Cosimo Uccello-Barretta, Gloria Balzano, Federica |
author_facet | Recchimurzo, Alessandra Micheletti, Cosimo Uccello-Barretta, Gloria Balzano, Federica |
author_sort | Recchimurzo, Alessandra |
collection | PubMed |
description | [Image: see text] The reaction of benzoyl isothiocyanate with (1R,2R)-1,2-bis(2-hydroxyphenyl)ethylenediamine afforded a new thiourea chiral solvating agent (CSA) with a very high ability to differentiate (1)H and (13)C NMR signals of simple amino acid derivatives, even at low concentrations. The enantiodiscrimination efficiency was higher with respect to that of the parent monomer, a thiourea derivative of 2-((1R)-1-aminoethyl)phenol, thus putting into light the relevance of the cooperativity between the two molecular portions of the dimer in a cleft conformation stabilized by interchain hydrogen bond interactions. An achiral base additive (DABCO or DMAP) played an active role in the chiral discrimination processes, mediating the interaction between the CSA and the enantiomeric mixtures. The chiral discrimination mechanism was investigated by NMR spectroscopy through the determination of complexation stoichiometries, association constants, and the stereochemistry of the diastereomeric solvates. |
format | Online Article Text |
id | pubmed-8279476 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-82794762021-07-15 A Dimeric Thiourea CSA for the Enantiodiscrimination of Amino Acid Derivatives by NMR Spectroscopy Recchimurzo, Alessandra Micheletti, Cosimo Uccello-Barretta, Gloria Balzano, Federica J Org Chem [Image: see text] The reaction of benzoyl isothiocyanate with (1R,2R)-1,2-bis(2-hydroxyphenyl)ethylenediamine afforded a new thiourea chiral solvating agent (CSA) with a very high ability to differentiate (1)H and (13)C NMR signals of simple amino acid derivatives, even at low concentrations. The enantiodiscrimination efficiency was higher with respect to that of the parent monomer, a thiourea derivative of 2-((1R)-1-aminoethyl)phenol, thus putting into light the relevance of the cooperativity between the two molecular portions of the dimer in a cleft conformation stabilized by interchain hydrogen bond interactions. An achiral base additive (DABCO or DMAP) played an active role in the chiral discrimination processes, mediating the interaction between the CSA and the enantiomeric mixtures. The chiral discrimination mechanism was investigated by NMR spectroscopy through the determination of complexation stoichiometries, association constants, and the stereochemistry of the diastereomeric solvates. American Chemical Society 2021-05-21 2021-06-04 /pmc/articles/PMC8279476/ /pubmed/34019407 http://dx.doi.org/10.1021/acs.joc.1c00340 Text en © 2021 The Authors. Published by American Chemical Society Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Recchimurzo, Alessandra Micheletti, Cosimo Uccello-Barretta, Gloria Balzano, Federica A Dimeric Thiourea CSA for the Enantiodiscrimination of Amino Acid Derivatives by NMR Spectroscopy |
title | A Dimeric Thiourea CSA
for the Enantiodiscrimination
of Amino Acid Derivatives by NMR Spectroscopy |
title_full | A Dimeric Thiourea CSA
for the Enantiodiscrimination
of Amino Acid Derivatives by NMR Spectroscopy |
title_fullStr | A Dimeric Thiourea CSA
for the Enantiodiscrimination
of Amino Acid Derivatives by NMR Spectroscopy |
title_full_unstemmed | A Dimeric Thiourea CSA
for the Enantiodiscrimination
of Amino Acid Derivatives by NMR Spectroscopy |
title_short | A Dimeric Thiourea CSA
for the Enantiodiscrimination
of Amino Acid Derivatives by NMR Spectroscopy |
title_sort | dimeric thiourea csa
for the enantiodiscrimination
of amino acid derivatives by nmr spectroscopy |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8279476/ https://www.ncbi.nlm.nih.gov/pubmed/34019407 http://dx.doi.org/10.1021/acs.joc.1c00340 |
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