This HTML5 document contains 51 embedded RDF statements represented using HTML+Microdata notation.

The embedded RDF content will be recognized by any processor of HTML5 Microdata.

Namespace Prefixes

PrefixIRI
dctermshttp://purl.org/dc/terms/
n10http://localhost/temp/predkladatel/
n14http://linked.opendata.cz/resource/domain/vavai/projekt/
n16http://linked.opendata.cz/resource/domain/vavai/vysledek/RIV%2F61989592%3A15310%2F14%3A33153620%21RIV15-MSM-15310___/
n19http://linked.opendata.cz/ontology/domain/vavai/
shttp://schema.org/
n6http://linked.opendata.cz/ontology/domain/vavai/riv/
rdfshttp://www.w3.org/2000/01/rdf-schema#
skoshttp://www.w3.org/2004/02/skos/core#
n12http://bibframe.org/vocab/
n2http://linked.opendata.cz/resource/domain/vavai/vysledek/
rdfhttp://www.w3.org/1999/02/22-rdf-syntax-ns#
n11http://linked.opendata.cz/ontology/domain/vavai/riv/klicoveSlovo/
n15http://linked.opendata.cz/ontology/domain/vavai/riv/duvernostUdaju/
xsdhhttp://www.w3.org/2001/XMLSchema#
n18http://linked.opendata.cz/ontology/domain/vavai/riv/aktivita/
n9http://linked.opendata.cz/ontology/domain/vavai/riv/jazykVysledku/
n17http://linked.opendata.cz/ontology/domain/vavai/riv/druhVysledku/
n7http://linked.opendata.cz/ontology/domain/vavai/riv/obor/
n8http://reference.data.gov.uk/id/gregorian-year/

Statements

Subject Item
n2:RIV%2F61989592%3A15310%2F14%3A33153620%21RIV15-MSM-15310___
rdf:type
skos:Concept n19:Vysledek
rdfs:seeAlso
http://www.sciencedirect.com/science/article/pii/S0021967314004956
dcterms:description
While aliphatic 2-hydroxyalkanoic acids have been more or less successfully enantioseparated with various chiral stationary phases by HPLC and GC, analogous applications on underivatized aliphatic 3-hydroxyalkanoic acids are completely absent in the scientific literature. With the aim of closing this gap, the enantioseparation of 3-hydroxybutyric acid, 3-hydroxydecanoic acid and 3-hydroxymyristic acid has been performed with two ion-exchange type chiral stationary phases (CSPs): one containing the anion-exchange type tert-butyl carbamoyl quinine chiral selector motif (Chiralpak QN-AX), and the other carrying the new zwitterionic variant based on trans-(S,S)-2-aminocyclohexanesulfonic acid-derivatized quinine carbamate (Chiralpak ZWIX(+)) as the chiral selector and enantiodiscriminating element, respectively. The zwitterionic enantiorecognition material provided better results in terms of enantioselectivity and resolution compared to the anion-exchanger CSP at reduced retention times due to the intramolecular counterion effect imposed by the sulfonic acid moiety and its competition with the 3-hydroxyalkanoic acid analyte for ionic interaction at the quininium-anion exchanger site. It is thus recommended as the CSP of first choice for enantioseparations of the class of aliphatic 3-hydroxyalkanoic acids. With use of polar organic eluent composed of ACN/MeOH/AcOH 95/5/0.05 (v/v/v), a good compromise in terms of analysis time and enantioresolution quality was accomplished. The major experimental variables have been investigated for optimization of the resolution and allowed to derive information on the enantiorecognition mechanism. Corresponding Chiralpak ZWIX(), based on pseudo-enantiomeric selector derived from quinidine and trans-(R,R)-2-aminocyclohexanesulfonic acid with opposite configurations provided reversed enantiomer elution orders. It has further to be stressed that these separations can be obtained with mass spectrometry compatible mobile phases. While aliphatic 2-hydroxyalkanoic acids have been more or less successfully enantioseparated with various chiral stationary phases by HPLC and GC, analogous applications on underivatized aliphatic 3-hydroxyalkanoic acids are completely absent in the scientific literature. With the aim of closing this gap, the enantioseparation of 3-hydroxybutyric acid, 3-hydroxydecanoic acid and 3-hydroxymyristic acid has been performed with two ion-exchange type chiral stationary phases (CSPs): one containing the anion-exchange type tert-butyl carbamoyl quinine chiral selector motif (Chiralpak QN-AX), and the other carrying the new zwitterionic variant based on trans-(S,S)-2-aminocyclohexanesulfonic acid-derivatized quinine carbamate (Chiralpak ZWIX(+)) as the chiral selector and enantiodiscriminating element, respectively. The zwitterionic enantiorecognition material provided better results in terms of enantioselectivity and resolution compared to the anion-exchanger CSP at reduced retention times due to the intramolecular counterion effect imposed by the sulfonic acid moiety and its competition with the 3-hydroxyalkanoic acid analyte for ionic interaction at the quininium-anion exchanger site. It is thus recommended as the CSP of first choice for enantioseparations of the class of aliphatic 3-hydroxyalkanoic acids. With use of polar organic eluent composed of ACN/MeOH/AcOH 95/5/0.05 (v/v/v), a good compromise in terms of analysis time and enantioresolution quality was accomplished. The major experimental variables have been investigated for optimization of the resolution and allowed to derive information on the enantiorecognition mechanism. Corresponding Chiralpak ZWIX(), based on pseudo-enantiomeric selector derived from quinidine and trans-(R,R)-2-aminocyclohexanesulfonic acid with opposite configurations provided reversed enantiomer elution orders. It has further to be stressed that these separations can be obtained with mass spectrometry compatible mobile phases.
dcterms:title
Direct enantioseparation of underivatized aliphatic 3-hydroxyalkanoic acids with a quinine-based zwitterionic chiral stationary phase Direct enantioseparation of underivatized aliphatic 3-hydroxyalkanoic acids with a quinine-based zwitterionic chiral stationary phase
skos:prefLabel
Direct enantioseparation of underivatized aliphatic 3-hydroxyalkanoic acids with a quinine-based zwitterionic chiral stationary phase Direct enantioseparation of underivatized aliphatic 3-hydroxyalkanoic acids with a quinine-based zwitterionic chiral stationary phase
skos:notation
RIV/61989592:15310/14:33153620!RIV15-MSM-15310___
n6:aktivita
n18:S n18:P
n6:aktivity
P(ED2.1.00/03.0058), P(GAP206/12/1150), S
n6:cisloPeriodika
OCT
n6:dodaniDat
n8:2015
n6:domaciTvurceVysledku
Pataj, Zoltán
n6:druhVysledku
n17:J
n6:duvernostUdaju
n15:S
n6:entitaPredkladatele
n16:predkladatel
n6:idSjednocenehoVysledku
11640
n6:idVysledku
RIV/61989592:15310/14:33153620
n6:jazykVysledku
n9:eng
n6:klicovaSlova
Natural compounds polar-organic mode; Cinchona-based zwitterionic chiral stationary phase; 3-Hydroxyalkanoic acids, liquid chromatography; Underivatized 3-hydroxycarboxylic acids; Enantiomer separation
n6:klicoveSlovo
n11:liquid%20chromatography n11:Enantiomer%20separation n11:Underivatized%203-hydroxycarboxylic%20acids n11:Natural%20compounds%20polar-organic%20mode n11:Cinchona-based%20zwitterionic%20chiral%20stationary%20phase n11:3-Hydroxyalkanoic%20acids
n6:kodStatuVydavatele
NL - Nizozemsko
n6:kontrolniKodProRIV
[8F8D8FC1624B]
n6:nazevZdroje
Journal of Chromatography A: Symposium Volumes
n6:obor
n7:CB
n6:pocetDomacichTvurcuVysledku
1
n6:pocetTvurcuVysledku
7
n6:projekt
n14:ED2.1.00%2F03.0058 n14:GAP206%2F12%2F1150
n6:rokUplatneniVysledku
n8:2014
n6:svazekPeriodika
1363
n6:tvurceVysledku
Sardella, Roccaldo Ianni, Federica Natalini, Benedatto Lämmerhofer, Michael Gross, Harald Lindner, Wolfgang Pataj, Zoltán
n6:wos
000343359100012
s:issn
0021-9673
s:numberOfPages
8
n12:doi
10.1016/j.chroma.2014.03.060
n10:organizacniJednotka
15310