The Enantiomeric Discrimination of 5-Hexyl-2-methyl-3,4-dihydro-2H-pyrrole by Sulfobutyl ether-β-cyclodextrin: A Case Study

1-Pyrrolines are important intermediates of active natural products, such as the 2,5-dialkyl-1-pyrroline derivatives found in fire ant venoms. Here, 5-hexyl-2-methyl-3,4-dihydro-2H-pyrrole was synthesized by the enzymatic transamination/cyclization of 2,5-undecadione, and enantiodifferenciation was...

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Autores principales: Kawano, Daniel F., Costa, Bruna Z., Romero-Orejón, Katherine L., Loureiro, Hugo C., de Jesus, Dosil P., Marsaioli, Anita J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8124876/
https://www.ncbi.nlm.nih.gov/pubmed/33947062
http://dx.doi.org/10.3390/molecules26092611
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author Kawano, Daniel F.
Costa, Bruna Z.
Romero-Orejón, Katherine L.
Loureiro, Hugo C.
de Jesus, Dosil P.
Marsaioli, Anita J.
author_facet Kawano, Daniel F.
Costa, Bruna Z.
Romero-Orejón, Katherine L.
Loureiro, Hugo C.
de Jesus, Dosil P.
Marsaioli, Anita J.
author_sort Kawano, Daniel F.
collection PubMed
description 1-Pyrrolines are important intermediates of active natural products, such as the 2,5-dialkyl-1-pyrroline derivatives found in fire ant venoms. Here, 5-hexyl-2-methyl-3,4-dihydro-2H-pyrrole was synthesized by the enzymatic transamination/cyclization of 2,5-undecadione, and enantiodifferenciation was successfully achieved by capillary electrophoresis with sulfobutyl ether- [Formula: see text]-cyclodextrin as the chiral selector. The rationale of the enantiomeric discrimination was based on the results of a docking simulation that revealed the higher affinity of (S)-5-hexyl-2-methyl-3,4-dihydro-2H-pyrrole for the sulfobutyl ether- [Formula: see text]-cyclodextrin.
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spelling pubmed-81248762021-05-17 The Enantiomeric Discrimination of 5-Hexyl-2-methyl-3,4-dihydro-2H-pyrrole by Sulfobutyl ether-β-cyclodextrin: A Case Study Kawano, Daniel F. Costa, Bruna Z. Romero-Orejón, Katherine L. Loureiro, Hugo C. de Jesus, Dosil P. Marsaioli, Anita J. Molecules Article 1-Pyrrolines are important intermediates of active natural products, such as the 2,5-dialkyl-1-pyrroline derivatives found in fire ant venoms. Here, 5-hexyl-2-methyl-3,4-dihydro-2H-pyrrole was synthesized by the enzymatic transamination/cyclization of 2,5-undecadione, and enantiodifferenciation was successfully achieved by capillary electrophoresis with sulfobutyl ether- [Formula: see text]-cyclodextrin as the chiral selector. The rationale of the enantiomeric discrimination was based on the results of a docking simulation that revealed the higher affinity of (S)-5-hexyl-2-methyl-3,4-dihydro-2H-pyrrole for the sulfobutyl ether- [Formula: see text]-cyclodextrin. MDPI 2021-04-29 /pmc/articles/PMC8124876/ /pubmed/33947062 http://dx.doi.org/10.3390/molecules26092611 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Kawano, Daniel F.
Costa, Bruna Z.
Romero-Orejón, Katherine L.
Loureiro, Hugo C.
de Jesus, Dosil P.
Marsaioli, Anita J.
The Enantiomeric Discrimination of 5-Hexyl-2-methyl-3,4-dihydro-2H-pyrrole by Sulfobutyl ether-β-cyclodextrin: A Case Study
title The Enantiomeric Discrimination of 5-Hexyl-2-methyl-3,4-dihydro-2H-pyrrole by Sulfobutyl ether-β-cyclodextrin: A Case Study
title_full The Enantiomeric Discrimination of 5-Hexyl-2-methyl-3,4-dihydro-2H-pyrrole by Sulfobutyl ether-β-cyclodextrin: A Case Study
title_fullStr The Enantiomeric Discrimination of 5-Hexyl-2-methyl-3,4-dihydro-2H-pyrrole by Sulfobutyl ether-β-cyclodextrin: A Case Study
title_full_unstemmed The Enantiomeric Discrimination of 5-Hexyl-2-methyl-3,4-dihydro-2H-pyrrole by Sulfobutyl ether-β-cyclodextrin: A Case Study
title_short The Enantiomeric Discrimination of 5-Hexyl-2-methyl-3,4-dihydro-2H-pyrrole by Sulfobutyl ether-β-cyclodextrin: A Case Study
title_sort enantiomeric discrimination of 5-hexyl-2-methyl-3,4-dihydro-2h-pyrrole by sulfobutyl ether-β-cyclodextrin: a case study
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8124876/
https://www.ncbi.nlm.nih.gov/pubmed/33947062
http://dx.doi.org/10.3390/molecules26092611
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