Simultaneous Discrimination and Quantification of Enantiomeric Amino Acids under Physiological Conditions by Chiral ¹⁹F NMR Tag
2022
Chen, Ya-Ting | Li, Bin | Chen, Jia-Liang | Su, Xun-Cheng
Enantiomeric analysis is of great significance in chemistry, chemical biology and pharmaceutical research. We herein propose a chiral ¹⁹F NMR tag containing an amino reactive NHS group to discriminate the enantiomeric amino acids under physiological conditions by NMR spectroscopy. The chiral ¹⁹F NMR tag readily forms stable amide products with the amino acids in aqueous solution. The stereospecific chemistry of enantiomeric amino acids is discriminated by a stereogenic carbon bonded with a ¹⁹F atom and is therefore decoded by the ¹⁹F reporter and manifested in the distinct ¹⁹F chemical shift. The chemical shift difference (ΔΔδ) of the chiral ¹⁹F NMR tag derived enantiomeric amino acids variants has a broad chemical shift range between −1.13 to 1.68 ppm, indicating the high sensitivity of the chiral ¹⁹F NMR tag to the stereospecific environment surrounding the individual amino acids. The distinguishable chemical shift produced by the chiral ¹⁹F NMR tag permits simultaneous discrimination and quantification of the enantiomeric amino acids in a mixture. The high fidelity of the chiral ¹⁹F NMR tag affords high-accuracy determination of the enantiomeric composition of amino acids by simple 1D NMR under physiological conditions.
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