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 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.

Direct enantiomeric discrimination through antisymmetric hyperfine coupling

A chirality-sensitive effect induced by antisymmetric hyperfine coupling, which lifts the intrinsic insensitivity of electron paramagnetic resonance spectroscopy to molecular chirality, is described.

Enantioselective GC Analysis of C3–Oxygenated p-Menthane type Indian Mentha Spicata var. Viridis ‘Ganga’ Essential Oil

Essential oil of Mentha spicata L. var. viridis ‘Ganga’, an indigenously developed variety, was chemically profiled using various gas chromatographic techniques. Piperitenone oxide was characterized as the most exclusive constituent (69.7%) along with a new C3–oxygenated p-menthane alcohol, diosphenolene (1.6%). Enantiomeric discrimination revealed (4 S)-(-)-limonene, ( R)-(-)-linalool and (1 S,2 S)-(+)-piperitenone oxide as predominant enantiomers. The oil contained mainly C3–oxygenated p-menthane monoterpenoids, which are distinctive of peppermint, instead of the characteristic C6–oxygenated class of spearmint. The present findings will aid in understanding the pathway and cause of C3-oxygenation in a spearmint taxon. The essential oil and pure piperitenone oxide showed growth inhibiting properties and thus, may be utilized in antifungal preparations for disease management of medicinal and aromatic plants.

Chiral Zn–salen complexes: a new class of fluorescent receptors for enantiodiscrimination of chiral amines

Highly efficient enantiomeric discrimination of chiral amines by fluorescent Zn–salen receptors is reported for the first time.

Synthesis of chiral R/S-pseudopeptide-based Cu(ii) & Zn(ii) complexes for use in targeted delivery for antitumor therapy: enantiomeric discrimination with CT-DNA and pBR322 DNA hydrolytic cleavage mechanism

The detailed mechanism of the hydrolytic cleavage pathway of 1S with pBR322 d DNA and the molecular docked model with DNA are shown below.