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

• Autoři: LABUTA Jan; ISHIHARA Shinsuke; ŠIKORSKÝ Tomáš; FUTERA Zdeněk; SHUNDO Atsuomi; HANYKOVÁ Lenka; BURDA Jaroslav; ARIGA Katsuhiko; HILL Jonathan P.
• Rok publikování: 2013
• Druh: Článek v odborném periodiku
• Časopis / Zdroj: NATURE COMMUNICATIONS
• Fakulta / Pracoviště MU: Středoevropský technologický institut
• www: http://www.nature.com/ncomms/2013/130717/ncomms3188/full/ncomms3188.html
• Doi: http://dx.doi.org/10.1038/ncomms3188
• Obor: Biochemie
• Klíčová slova: ENANTIOMERIC EXCESS; ABSOLUTE-CONFIGURATION; MOLECULAR RECOGNITION; PORPHYRIN; ACID; AMPLIFICATION; COMPLEXES; MECHANISM; ALCOHOLS; MEMORY
• Popis: 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 H-1 NMR spectra.

Související projekty

• CEITEC - středoevropský technologický institut