Green Strategies for the Preparation of Enantiomeric 5–8-Membered Carbocyclic β-Amino Acid Derivatives through CALB-Catalyzed Hydrolysis

Candida antarctica lipase B-catalyzed hydrolysis of carbocyclic 5–8-membered cis β-amino esters was carried out in green organic media, under solvent-free and ball-milling conditions. In accordance with the high enantioselectivity factor (E > 200) observed in organic media, the preparative-scale...

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Autores principales: Shahmohammadi, Sayeh, Faragó, Tünde, Palkó, Márta, Forró, Enikő
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9032184/
https://www.ncbi.nlm.nih.gov/pubmed/35458798
http://dx.doi.org/10.3390/molecules27082600
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author Shahmohammadi, Sayeh
Faragó, Tünde
Palkó, Márta
Forró, Enikő
author_facet Shahmohammadi, Sayeh
Faragó, Tünde
Palkó, Márta
Forró, Enikő
author_sort Shahmohammadi, Sayeh
collection PubMed
description Candida antarctica lipase B-catalyzed hydrolysis of carbocyclic 5–8-membered cis β-amino esters was carried out in green organic media, under solvent-free and ball-milling conditions. In accordance with the high enantioselectivity factor (E > 200) observed in organic media, the preparative-scale resolutions of β-amino esters were performed in tBuOMe at 65 °C. The unreacted β-amino ester enantiomers (1R,2S) and product β-amino acid enantiomers (1S,2R) were obtained with modest to excellent enantiomeric excess (ee) values (ee(s) > 62% and ee(p) > 96%) and in good chemical yields (>25%) in one or two steps. The enantiomers were easily separated by organic solvent/H(2)O extraction.
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spelling pubmed-90321842022-04-23 Green Strategies for the Preparation of Enantiomeric 5–8-Membered Carbocyclic β-Amino Acid Derivatives through CALB-Catalyzed Hydrolysis Shahmohammadi, Sayeh Faragó, Tünde Palkó, Márta Forró, Enikő Molecules Article Candida antarctica lipase B-catalyzed hydrolysis of carbocyclic 5–8-membered cis β-amino esters was carried out in green organic media, under solvent-free and ball-milling conditions. In accordance with the high enantioselectivity factor (E > 200) observed in organic media, the preparative-scale resolutions of β-amino esters were performed in tBuOMe at 65 °C. The unreacted β-amino ester enantiomers (1R,2S) and product β-amino acid enantiomers (1S,2R) were obtained with modest to excellent enantiomeric excess (ee) values (ee(s) > 62% and ee(p) > 96%) and in good chemical yields (>25%) in one or two steps. The enantiomers were easily separated by organic solvent/H(2)O extraction. MDPI 2022-04-18 /pmc/articles/PMC9032184/ /pubmed/35458798 http://dx.doi.org/10.3390/molecules27082600 Text en © 2022 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
Shahmohammadi, Sayeh
Faragó, Tünde
Palkó, Márta
Forró, Enikő
Green Strategies for the Preparation of Enantiomeric 5–8-Membered Carbocyclic β-Amino Acid Derivatives through CALB-Catalyzed Hydrolysis
title Green Strategies for the Preparation of Enantiomeric 5–8-Membered Carbocyclic β-Amino Acid Derivatives through CALB-Catalyzed Hydrolysis
title_full Green Strategies for the Preparation of Enantiomeric 5–8-Membered Carbocyclic β-Amino Acid Derivatives through CALB-Catalyzed Hydrolysis
title_fullStr Green Strategies for the Preparation of Enantiomeric 5–8-Membered Carbocyclic β-Amino Acid Derivatives through CALB-Catalyzed Hydrolysis
title_full_unstemmed Green Strategies for the Preparation of Enantiomeric 5–8-Membered Carbocyclic β-Amino Acid Derivatives through CALB-Catalyzed Hydrolysis
title_short Green Strategies for the Preparation of Enantiomeric 5–8-Membered Carbocyclic β-Amino Acid Derivatives through CALB-Catalyzed Hydrolysis
title_sort green strategies for the preparation of enantiomeric 5–8-membered carbocyclic β-amino acid derivatives through calb-catalyzed hydrolysis
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9032184/
https://www.ncbi.nlm.nih.gov/pubmed/35458798
http://dx.doi.org/10.3390/molecules27082600
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