NMR spectroscopic detection of chirality and enantiopurity in referenced systems without formation of diastereomers

Jan Labuta, Shinsuke Ishihara, Tomáš Šikorský, Zdeněk Futera, Atsuomi Shundo, Lenka Hanyková, Jaroslav V. Burda, Katsuhiko Ariga and Jonathan P. Hill ()
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Jan Labuta: International Center for Materials Nanoarchitectonics (MANA), National Institute for Materials Science (NIMS), 1-1 Namiki
Shinsuke Ishihara: International Center for Materials Nanoarchitectonics (MANA), National Institute for Materials Science (NIMS), 1-1 Namiki
Tomáš Šikorský: CEITEC—Central European Institute of Technology, Masaryk University
Zdeněk Futera: Charles University in Prague, Faculty of Mathematics and Physics, Ke Karlovu 3, 121 16 Prague 2, Czech Republic
Atsuomi Shundo: International Center for Materials Nanoarchitectonics (MANA), National Institute for Materials Science (NIMS), 1-1 Namiki
Lenka Hanyková: Charles University in Prague, Faculty of Mathematics and Physics, V Holešovičkách 2, 180 00 Prague 8, Czech Republic
Jaroslav V. Burda: Charles University in Prague, Faculty of Mathematics and Physics, Ke Karlovu 3, 121 16 Prague 2, Czech Republic
Katsuhiko Ariga: International Center for Materials Nanoarchitectonics (MANA), National Institute for Materials Science (NIMS), 1-1 Namiki
Jonathan P. Hill: International Center for Materials Nanoarchitectonics (MANA), National Institute for Materials Science (NIMS), 1-1 Namiki

Nature Communications, 2013, vol. 4, issue 1, 1-8

Abstract: Abstract Enantiomeric excess of chiral compounds is a key parameter that determines their activity or therapeutic action. The current paradigm for rapid measurement of enantiomeric excess using NMR is based on the formation of diastereomeric complexes between the chiral analyte and a chiral resolving agent, leading to (at least) two species with no symmetry relationship. Here we report an effective method of enantiomeric excess determination using a symmetrical achiral molecule as the resolving agent, which is based on the complexation with analyte (in the fast exchange regime) without the formation of diastereomers. The use of N,N′-disubstituted oxoporphyrinogen as the resolving agent makes this novel method extremely versatile, and appropriate for various chiral analytes including carboxylic acids, esters, alcohols and protected amino acids using the same achiral molecule. The model of sensing mechanism exhibits a fundamental linear response between enantiomeric excess and the observed magnitude of induced chemical shift non-equivalence in the 1H NMR spectra.

Date: 2013
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DOI: 10.1038/ncomms3188

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