The Enantiomeric Discrimination of 5-Hexyl-2-methyl-3,4-dihydro-2H-pyrrole by Sulfobutyl ether-β-cyclodextrin: A Case Study
| Autor: | Katherine L. Romero-Orejón, Bruna Z. Costa, Anita J. Marsaioli, Dosil Pereira de Jesus, Daniel Fábio Kawano, Hugo Campos Loureiro |
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| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Models
Molecular Transamination Molecular Conformation Pharmaceutical Science Organic chemistry Pyrroline Chemistry Techniques Synthetic Molecular Dynamics Simulation Article Analytical Chemistry chemistry.chemical_compound Capillary electrophoresis QD241-441 sulfotbutyl ether-β-cyclodextrin Sulfobutyl ether β cyclodextrin Drug Discovery Humans Pyrroles Physical and Theoretical Chemistry Pyrrole chemistry.chemical_classification Cyclodextrins Molecular Structure enantiodifferenciation beta-Cyclodextrins Electrophoresis Capillary Combinatorial chemistry Molecular Docking Simulation Enzyme chemistry Chemistry (miscellaneous) Docking (molecular) docking Molecular Medicine chiral capillary electrophoresis Enantiomer pyrroline |
| Zdroj: | Molecules Volume 26 Issue 9 Molecules, Vol 26, Iss 2611, p 2611 (2021) |
| ISSN: | 1420-3049 |
| DOI: | 10.3390/molecules26092611 |
| Popis: | 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-β-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-β-cyclodextrin. |
| Databáze: | OpenAIRE |
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