LABUTA, Jan, Shinsuke ISHIHARA, Tomáš ŠIKORSKÝ, Zdeněk FUTERA, Atsuomi SHUNDO, Lenka HANYKOVÁ, Jaroslav BURDA, Katsuhiko ARIGA and Jonathan P. HILL. NMR spectroscopic detection of chirality and enantiopurity in referenced systems without formation of diastereomers. NATURE COMMUNICATIONS. LONDON: NATURE PUBLISHING GROUP, 2013, vol. 4, July, p. "nestránkováno", 8 pp. ISSN 2041-1723. Available from: https://dx.doi.org/10.1038/ncomms3188. |
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@article{1122076, author = {Labuta, Jan and Ishihara, Shinsuke and Šikorský, Tomáš and Futera, Zdeněk and Shundo, Atsuomi and Hanyková, Lenka and Burda, Jaroslav and Ariga, Katsuhiko and Hill, Jonathan P.}, article_location = {LONDON}, article_number = {July}, doi = {http://dx.doi.org/10.1038/ncomms3188}, keywords = {ENANTIOMERIC EXCESS; ABSOLUTE-CONFIGURATION; MOLECULAR RECOGNITION; PORPHYRIN; ACID; AMPLIFICATION; COMPLEXES; MECHANISM; ALCOHOLS; MEMORY}, language = {eng}, issn = {2041-1723}, journal = {NATURE COMMUNICATIONS}, title = {NMR spectroscopic detection of chirality and enantiopurity in referenced systems without formation of diastereomers}, url = {http://www.nature.com/ncomms/2013/130717/ncomms3188/full/ncomms3188.html}, volume = {4}, year = {2013} }
TY - JOUR ID - 1122076 AU - Labuta, Jan - Ishihara, Shinsuke - Šikorský, Tomáš - Futera, Zdeněk - Shundo, Atsuomi - Hanyková, Lenka - Burda, Jaroslav - Ariga, Katsuhiko - Hill, Jonathan P. PY - 2013 TI - NMR spectroscopic detection of chirality and enantiopurity in referenced systems without formation of diastereomers JF - NATURE COMMUNICATIONS VL - 4 IS - July SP - "nestránkováno" EP - "nestránkováno" PB - NATURE PUBLISHING GROUP SN - 20411723 KW - ENANTIOMERIC EXCESS KW - ABSOLUTE-CONFIGURATION KW - MOLECULAR RECOGNITION KW - PORPHYRIN KW - ACID KW - AMPLIFICATION KW - COMPLEXES KW - MECHANISM KW - ALCOHOLS KW - MEMORY UR - http://www.nature.com/ncomms/2013/130717/ncomms3188/full/ncomms3188.html L2 - http://www.nature.com/ncomms/2013/130717/ncomms3188/full/ncomms3188.html N2 - 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. ER -
LABUTA, Jan, Shinsuke ISHIHARA, Tomáš ŠIKORSKÝ, Zdeněk FUTERA, Atsuomi SHUNDO, Lenka HANYKOVÁ, Jaroslav BURDA, Katsuhiko ARIGA and Jonathan P. HILL. NMR spectroscopic detection of chirality and enantiopurity in referenced systems without formation of diastereomers. \textit{NATURE COMMUNICATIONS}. LONDON: NATURE PUBLISHING GROUP, 2013, vol.~4, July, p.~''nestránkováno'', 8 pp. ISSN~2041-1723. Available from: https://dx.doi.org/10.1038/ncomms3188.
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