Catalytic Enantioselective Sulfoxidation of Functionalized Thioethers Mediated by Aspartic Acid-Containing Peptides.
Susannah E HuthNicolò TampelliniMaria D GuerreroScott J MillerPublished in: Organic letters (2024)
A peptide-catalyzed enantioselective oxidation of sulfides to yield pharmaceutically relevant chiral sulfoxides is reported. Experimental evidence suggesting that a hydrogen bond-donating moiety must be present in the substrate to achieve high levels of enantioinduction is supported by computational modeling of transition states. These models also indicate that dual points of contact between the peptidic catalyst and substrate are likely responsible for the formation of one desired sulfoxide in 94:6 er.
Keyphrases
- room temperature
- visible light
- ionic liquid
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- quantum dots
- structural basis
- hydrogen peroxide
- highly efficient
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- endoplasmic reticulum
- molecularly imprinted
- metal organic framework
- carbon dioxide
- gold nanoparticles
- mass spectrometry
- simultaneous determination
- solid phase extraction
- liquid chromatography