Unknown

Dataset Information

0

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

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-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.

SUBMITTER: Kawano DF 

PROVIDER: S-EPMC8124876 | biostudies-literature | 2021 Apr

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

The Enantiomeric Discrimination of 5-Hexyl-2-methyl-3,4-dihydro-2<i>H</i>-pyrrole by Sulfobutyl ether-β-cyclodextrin: A Case Study.

Kawano Daniel F DF   Costa Bruna Z BZ   Romero-Orejón Katherine L KL   Loureiro Hugo C HC   de Jesus Dosil P DP   Marsaioli Anita J AJ  

Molecules (Basel, Switzerland) 20210429 9

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-2<i>H</i>-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 do  ...[more]

Similar Datasets

Unknown (3R,4S)-3,4-Isopropyl-idenedioxy-3,4-dihydro-2H-pyrrole 1-oxide.
| S-EPMC3089370 | biostudies-literature
Unknown (3R,4S)-3,4-Isopropylidenedioxy-5-phenylsulfonylmethyl-3,4-dihydro-2H-pyrrole 1-oxide.
| S-EPMC3089343 | biostudies-literature
Unknown 5-(3-Chloro-phen-yl)-2-phenyl-3,4-dihydro-2H-pyrrole.
| S-EPMC3009276 | biostudies-other
Unknown 2,2,7-Trichloro-3,4-dihydro-naphthalen-1(2H)-one.
| S-EPMC2969904 | biostudies-literature
Unknown 3,4-Dihydro-1,4-benzothia-zepin-5(2H)-one.
| S-EPMC2915184 | biostudies-literature
Unknown rac-2-Iodo-3,4-dihydro-naphthalen-1(2H)-one.
| S-EPMC2971913 | biostudies-literature
Unknown 7-Meth-oxy-3,4-dihydro-naphthalen-1(2H)-one.
| S-EPMC3152045 | biostudies-literature
Unknown Voriconazole Eye Drops: Enhanced Solubility and Stability through Ternary Voriconazole/Sulfobutyl Ether β-Cyclodextrin/Polyvinyl Alcohol Complexes.
| S-EPMC9917179 | biostudies-literature
Unknown 3,3'-Ethyl-enebis(3,4-dihydro-6-chloro-2H-1,3-benzoxazine).
| S-EPMC2979041 | biostudies-literature
Unknown 3,3-Dimethyl-9-phenyl-3,4-dihydro-acridin-1(2H)-one.
| S-EPMC2962177 | biostudies-literature