Chiral Recognition by Dissolution DNP NMR Spectroscopy of 13C-Labeled dl-Methionine

Monteagudo, Eva, Albert Virgili, Teodor Parella, and Míriam Pérez-Trujillo. “Chiral Recognition by Dissolution DNP NMR Spectroscopy of 13C-Labeled Dl-Methionine.” Analytical Chemistry 89, no. 9 (May 2, 2017): 4939–44.

A method based on d-DNP NMR spectroscopy to study chiral recognition is described for the first time. The enantiodifferentiation of a racemic metabolite in a millimolar aqueous solution using a chiral solvating agent was performed. Hyperpolarized 13C-labeled DL-methionine enantiomers were differently observed with a single-scan 13C NMR experiment, while the chiral auxiliary at thermal equilibrium remained unobserved. The method developed entails a step forward in the chiral recognition of small molecules by NMR spectroscopy, opening new possibilities in situations where the sensitivity is limited; e.g. when a low concentration of analyte is available or when the measurement of an insensitive nucleus, like 13C, is required. The advantages and current limitations of the developed method, as well as, future perspectives are discussed.

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