Chirality plays an essential role in the existence and continuation of life. Chiral analysis of biological molecules is a significant step in various research fields including pharmacological science, drug development as well as flavor science. Vibrational Circular Dichroism (VCD) measures differential absorption of left-versus-right circularly polarized IR radiation by molecular vibrational transitions, which have both advantages of CD and IR features. VCD is an emerging reliable technique for stereochemical analyses in the field of life sciences as well as material sciences in combination with DFT theoretical calculation. VCD has great advantages toward chiral analysis of flavor compounds for several reasons: (i) Flavor compounds are generally small molecules, and VCD has a great advantage toward relatively small molecules since limitation of computational calculation power. (ii) Flavor compounds are likely rigid in terms of their conformations, and VCD spectrum is dependent on their conformations, small numbers of conformations are advantage for the accurate VCD theoretical calculation. (iii) Flavor compounds have less functional groups, in some case only C and H. VCD technique does not require some special functional groups such as a sec- hydroxyl group in case of the Mosher method. We have succeeded in application of the VCD technique to determine of their absolute configurations of flavorous furanones, which did not go well with other standard chiral analytical methods.

Vibrational CD spectroscopy as a powerful tool for chiral analysis of flavor compounds

248th National Meeting (2014)

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