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

Author(s)

Kawano, Daniel F. ; Costa, Bruna Z. ; Romero-Orejon, Katherine L. ; Loureiro, Hugo C. ; de Jesus, Dosil P. ; Marsaioli, Anita J.

• Document type: Journal article
• Source: Molecules; v. 26, n. 9, p. 7-pg., 2021-05-01.

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-beta-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-beta-cyclodextrin. (AU)

• FAPESP's process: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
• Grantee: Arlene Gonçalves Corrêa
• Support Opportunities: Research Grants - Research Centers in Engineering Program
• FAPESP's process: 18/08585-1 - Design and synthesis of new phospholipids that selectively induce the apoptosis of tumor cells via lipid rafts
• Grantee: Daniel Fábio Kawano
• Support Opportunities: Regular Research Grants
• FAPESP's process: 13/22127-2 - Development of novel materials strategic for integrated analytical devices
• Grantee: Lauro Tatsuo Kubota
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 14/50867-3 - INCT 2014: National Institute of Science and Technology in Bioanalysis
• Grantee: Marco Aurelio Zezzi Arruda
• Support Opportunities: Research Projects - Thematic Grants