Attracting Enantiomers: Chiral Analytes That Are Simultaneously Shift Reagents Allow Rapid Screening of Enantiomeric Ratios by NMR Spectroscopy.
Golo StorchMaren HaasOliver TrappPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2017)
The rapid and direct determination of enantiomeric ratios is of increasing interest due to the significantly reduced effort compared to chromatographic methods and the large number of analytes, for instance in enantioselective catalysis. Current strategies include colorimetric assays, (a)chiral solvating reagents for NMR spectroscopy and metal complexes for CD sensing. We report the determination of enantiomeric ratios based on the self-induced diastereomeric anisochronism (SIDA) effect. Alanine derivatives that represent chiral products of enantioselective catalysis, such as the well-established hydrogenation of dehydroamino acids, were investigated. The SIDA effect was significantly enhanced by attachment of 3,5-dinitrobenzoyl π-π interactions sites. This simple modification enabled simultaneous determination of enantiomeric ratios and conversions by NMR spectroscopy.
Keyphrases
- capillary electrophoresis
- simultaneous determination
- mass spectrometry
- solid phase extraction
- liquid chromatography
- liquid chromatography tandem mass spectrometry
- high performance liquid chromatography
- tandem mass spectrometry
- molecularly imprinted
- ionic liquid
- gold nanoparticles
- high throughput
- high glucose
- loop mediated isothermal amplification
- hydrogen peroxide
- oxidative stress
- fluorescent probe
- high resolution
- atomic force microscopy
- diabetic rats
- gas chromatography
- endothelial cells
- single molecule
- label free