Enantiomeric NMR discrimination of carboxylic acids using actinomycin D as a chiral solvating agent

Literature Information

Publication Date 2019-01-17
DOI 10.1039/C8OB03012J
Impact Factor 3.876
Authors

Liwen Bai, Pian Chen, Jiangxia Xiang, Jiarui Sun, Xinxiang Lei


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Abstract

Actinomycin D (Act-D) is a biologically important polypeptide antibiotic clinically used to treat several malignant tumors. Herein, we extended its hitherto-unexplored application as an applicable chiral solvating agent (CSA) for the rapid enantiomeric determination of different chiral carboxylic acids in deuterated chloroform by 1H NMR spectroscopy. Notable enantiodiscrimination with well-splitting α-H or α-CH3 resonance signals of the enantiomers of carboxylic acids were achieved without significant interference from Act-D. To check its applicability for the determination of enantiomeric excess (ee) values, various mandelic acid (MA) samples were determined and compared with the observed ones, resulting in an excellent linear relationship. To our knowledge, this is the first example of using a natural antibiotic compound as a CSA to achieve chiral recognition for carboxylic acids.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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