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NMR analysis of the enantiomeric purity of chiral diols by a new chiral boron agent.

ABSTRACT: A new boric agent with bridged structure, boric acid D, was first synthesized and used as an excellent chiral derivative agent for highly efficient enantiodiscrimination of various diols. The derivatization reaction is fast and complete, easy to operate and has high accuracy in measurement of ee values. The characteristic split NMR signals are well-distinguishable with a large chemical shift nonequivalence (up to 0.39 ppm).

SUBMITTER: Zhang X

PROVIDER: S-EPMC8981704 | biostudies-literature | 2022 Feb

REPOSITORIES: biostudies-literature

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NMR analysis of the enantiomeric purity of chiral diols by a new chiral boron agent.

Zhang Xuebo X Xu Jing J Sun Zhaofeng Z Bian Guangling G Song Ling L

RSC advances 20220208 8

A new boric agent with bridged structure, boric acid D, was first synthesized and used as an excellent chiral derivative agent for highly efficient enantiodiscrimination of various diols. The derivatization reaction is fast and complete, easy to operate and has high accuracy in measurement of ee values. The characteristic split NMR signals are well-distinguishable with a large chemical shift nonequivalence (up to 0.39 ppm). ...[more]

PMID: 35425523

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Project description:Chirality is an important property of molecules. The study of biological activity and toxicity of chiral molecules has important theoretical and practical significance for toxicology, pharmacology, and environmental science. The toxicological significance of chiral ionic liquids (ILs) has not been well revealed. In the present study, the enantiomeric joint toxicities of four pairs of chiral ILs 1-alkyl-3-methylimidazolium lactate to Allivibrio fischeri were systematically investigated by using a comprehensive approach including the co-toxicity coefficient (CTC) integrated with confidence interval (CI) method (CTCICI), concentration-response curve (CRC), and isobole analysis. The direct equipartition ray (EquRay) design was used to design five binary mixtures of enantiomers according to molar ratios of 1:5, 2:4, 3:3, 4:2, and 5:1. The toxicities of chiral ILs and their mixtures were determined using the microplate toxicity analysis (MTA) method. Concentration addition (CA) and independent action (IA) were used as the additive reference models to construct the predicted CRC and isobole of mixtures. On the whole, there was an enantioselective toxicity difference between [BMIM]D-Lac and [BMIM]L-Lac, and [HMIM]D-Lac and [HMIM]L-Lac, while no enantioselective toxicity difference was observed for [EMIM]D-Lac and [EMIM]L-Lac, and [OMIM]D-Lac and [OMIM]L-Lac. Thereinto, the enantiomer mixtures of [BMIM]D-Lac and [BMIM]L-Lac, and [HMIM]D-Lac and [HMIM]L-Lac presented antagonistic action, and the enantiomer mixtures of [EMIM]D-Lac and [EMIM]L-Lac, and [OMIM]D-Lac and [OMIM]L-Lac overall presented additive action. Moreover, the greatest antagonistic toxicity interaction occurred at the equimolar ratio of enantiomers. Based on these results, we proposed two hypotheses, (1) chiral molecules with enantioselective toxicity difference tended to produce toxicity interactions, (2) the highest or lowest toxicity was usually at the equimolar ratio and its adjacent ratio for the enantiomer mixture. These hypotheses will need to be further validated by other enantiomer mixtures.

Dataset Information

NMR analysis of the enantiomeric purity of chiral diols by a new chiral boron agent.

Publications

NMR analysis of the enantiomeric purity of chiral diols by a new chiral boron agent.

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