The Enantiomeric Discrimination of 5-Hexyl-2-methyl-3,4-dihydro-2H-pyrrole by Sulfobutyl ether-β-cyclodextrin: A Case Study |
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| Authors: | Daniel F. Kawano,Bruna Z. Costa,Katherine L. Romero-Orejó n,Hugo C. Loureiro,Dosil P. de Jesus,Anita J. Marsaioli |
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| Affiliation: | 1.Institute of Chemistry, University of Campinas, Campinas 13083-861, SP, Brazil; (D.F.K.); (B.Z.C.); (K.L.R.-O.); (D.P.d.J.);2.Faculty of Pharmaceutical Sciences, University of Campinas, Campinas 13083-871, SP, Brazil |
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| Abstract: | 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--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--cyclodextrin. |
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| Keywords: | chiral capillary electrophoresis, pyrroline, enantiodifferenciation, docking, sulfotbutyl ether-β -cyclodextrin |
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