Putting chirality to work: the strategy of chiral switches

Agranat, Israel; Caner, Hava; Caldwell, John

doi:10.1038/nrd915

Cited by 558 publications

(482 citation statements)

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“…Considerable differences in the toxicological, pharmacological, or pharmacokinetic properties of individual enantiomers also highlight the importance of assessing the stereochemical purity of a compound in the cosmetic and fragrance industries and environmental analysis. In an effort to eliminate potential toxic side effects, most approved new chiral chemicals are marketed worldwide as singleenantiomer drugs rather than as racemates [4]. Thus, as a consequence of policies of the Food and Drug Administration (FDA), accurate determination of enantiomeric composition and purity is necessary for production of drugs containing only the therapeutically active enantiomers, which requires sensitive and accurate analytical techniques [5].…”

Section: Introductionmentioning

confidence: 99%

Determination of Enantiomeric Compositions of Analytes Using Novel Fluorescent Chiral Molecular Micelles and Steady State Fluorescence Measurements

et al. 2007

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Novel fluorescent chiral molecular micelles (FCMMs) were synthesized, characterized, and employed as chiral selectors for enantiomeric recognition of non-fluorescent chiral molecules using steady state fluorescence spectroscopy. The sensitivity of the fluorescence technique allowed for investigation of low concentrations of chiral selector (3.0×10 −5 M) and analyte (5.0×10 −6 M) to be used in these studies. The chiral interactions of glucose, tartaric acid, and serine in the presence of, and poly(sodium N-undecanoyl-L-phenylalininate) [poly-SUF] were based on diastereomeric complex formation. Poly-L-SUW had a significant fluorescence emission spectral difference as compared to poly-L-SUY and poly-L-SUF for the enantiomeric recognition of glucose, tartaric acid, and serine. Studies with the hydrophobic molecule α-pinene suggested that poly-L-SUY and poly-L-SUF had better chiral discrimination ability for hydrophobic analytes as compared to hydrophilic analytes. Partial-least-squares regression modeling (PLS-1) was used to correlate changes in the fluorescence emission spectra of poly-L-SUW due to varying enantiomeric compositions of glucose, tartaric acid, and serine for a set of calibration samples. Validation of the calibration regression models was determined by use of a set of independently prepared samples of the same concentration of chiral selector and analyte with varying enantiomeric composition. Prediction ability was evaluated by use of the root-mean-square percent relative error (RMS%RE) and was found to range from 2.04 to 4.06%.

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Section: Introductionmentioning

confidence: 99%

Determination of Enantiomeric Compositions of Analytes Using Novel Fluorescent Chiral Molecular Micelles and Steady State Fluorescence Measurements

et al. 2007

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“…Its implications in biochemistry are far reaching since most biomaterials exhibit predominance for a single enantiomer. Hence the importance of the synthesis and separation of pure enantiomers has been well recognized [2]. Heterogeneous catalytic processes for enantioselective synthesis have important advantages over conventional homogeneous ones [3].…”

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confidence: 99%

Atom-Specific Identification of Adsorbed Chiral Molecules by Photoemission

et al. 2005

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The study of chiral adsorbed molecules is important for an analysis of enantioselectivity in heterogeneous catalysis. Here we show that such molecules can be identified through circular dichroism in corelevel photoemission arising from the chiral carbon atoms in stereoisomers of 2,3-butanediol molecules adsorbed on Si(100), using circularly polarized x rays. The asymmetry in the carbon 1s intensity excited by right and left circularly polarized light is readily observed, and changes sign with the helicity of the radiation or handedness of the enantiomers; it is absent in the achiral form of the molecule. This observation demonstrates the possibility of determining molecular chirality in the adsorbed phase.

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“…Clinical tests indicate that the replacement of racemate by a single active enantiomer of pharmaceutical allows to use of lower doses of drugs, increasing the therapeutic efficacy of individual doses. It helps to avoid possible harmful interactions with other drugs, to minimize the differences in drug metabolism between species and reduce the toxicity caused by supplementation of inactive isomers (Agranat et al, 2002;Baumann et al, 2002). There has been a trend towards to ensure that pharmaceuticals that were invented, approved and marketed as a racemate or a mixture of diastereomers, have been re-marketed as single enantiomers.…”

Section: Introductionmentioning

confidence: 99%