Anisotropic chiral interactions measurements

Analysis of natural abundance deuterium distribution in organic molecules, an important step in the study of kinetic isotope effects associated with enzyme-catalyzed reactions, by the use of chiral anisotropic media has been explored. An aspect of this analysis is the discrimination of the enantiotopic deuterons in prochiral molecules and the quantification of isotopic fractionation on methylene prostereogenic sites. Towards this an approach has been presented which is based on the use of natural abundance 2-dimensional NMR experiments on solutes oriented by chiral liquid crystalline solvents and the separation of the deuterium signals based on the quadrupolar interaction. The case of 1,1 -bis(phenylthio)hexane derived by cleavage from methyl linoleate of safflower has been used to illustrate the method with (D/H)pro-R and (D/H)pro-S measured at the same methylene position of a fatty acid chain. Enantiomers of water soluble materials can be observed using deuterium NMR spectroscopy in the lyotropic mesophase formed by glucopon/hexanol/buffered water. ... 

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