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Simpler way to determine chirality A new method should make it easier to determine the absolute configuration of compounds by NMR spectroscopy. Currently, a reagent called a chiral auxiliary is reacted with a chiral compound of unknown configuration to form a diastereomer. HPLC-NMR can then be used to separate components of the reaction mixture and identify the configuration of the diastereomer, making it possible to deduce the configuration of the unknown. Ricardo Riguera and coworkers at the University of Santiago de Compostela, in Spain, have now developed solid support-bound chiral auxiliaries that make it possible to carry out the process by mixing and shaking in an NMR tube in as little as five minutes, without a separate workup or HPLC separation. They demonstrated the technique on chiral amines and alcohols [Org. Lett., 5, 2979 (2003)]. It's an "ingenious simplification" of current methodology, comments natural products chemist William H. Gerwick of Oregon State University, Corvallis. "This approach, and others under development, will make even more routine what has historically been one of the most difficult elements of structural analysis." Potential applications include quality control of chiral pharmaceuticals. |
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