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

J 2013

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

LABUTA, Jan, Shinsuke ISHIHARA, Tomáš ŠIKORSKÝ, Zdeněk FUTERA, Atsuomi SHUNDO et. al.

Basic information

Original name

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

Authors

LABUTA, Jan (203 Czech Republic), Shinsuke ISHIHARA (392 Japan), Tomáš ŠIKORSKÝ (703 Slovakia, guarantor, belonging to the institution), Zdeněk FUTERA (203 Czech Republic), Atsuomi SHUNDO (392 Japan), Lenka HANYKOVÁ (203 Czech Republic), Jaroslav BURDA (203 Czech Republic), Katsuhiko ARIGA (392 Japan) and Jonathan P. HILL (392 Japan)

Edition

NATURE COMMUNICATIONS, LONDON, NATURE PUBLISHING GROUP, 2013, 2041-1723

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10600 1.6 Biological sciences

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 10.742

RIV identification code

RIV/00216224:14740/13:00069288

Organization unit

Central European Institute of Technology

DOI

http://dx.doi.org/10.1038/ncomms3188

UT WoS

000323716600024

Keywords in English

ENANTIOMERIC EXCESS; ABSOLUTE-CONFIGURATION; MOLECULAR RECOGNITION; PORPHYRIN; ACID; AMPLIFICATION; COMPLEXES; MECHANISM; ALCOHOLS; MEMORY

Abstract

V originále

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.

Links

ED1.1.00/02.0068, research and development project

Name: CEITEC - central european institute of technology

Citovat

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.

@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.

Detailed Information on Publication Record