Abstract:
:Supercritical fluid chromatography (SFC) is already used for enantioseparation in the pharmaceutical industry, but it is rarely used for the separation of chiral pesticides. Comparing with high performence liquid chromatography, SFC uses much more environmnetal friendly and economic mobile phase, supercritical CO2 . In our work, the enantioseparation of an amide herbicide, napropamide, using three different polysaccharide-type chiral stationary phases (CSPs) in SFC was investigated. By studying the effect of different CSPs, organic modifiers, temperature, back-pressure regulator pressures, and flow rates for the enantioseparation of napropamide, we established a rapid and green method for enantioseparation that takes less than 2 minutes: The column was CEL2, the mobile phase was CO2 with 20% 2-propanol, and the flow rate was 2.0 mL/min. We found that CEL2 demonstrated the strongest resolution capability. Acetonitrile was favored over alcoholic solvents when the CSP was amylose and 2-propanol was the best choice when using cellulose. When the concentration of the modifiers or the flow rate was decreased, resolutions and analysis times increased concurrently. The temperature and back-pressure regulator pressure exhibited only minor influences on the resolution and analysis time of the napropamide enantioseparations with these chiral columns. The molecular docking analysis provided a deeper insight into the interactions between the enantiomers and the CSPs at the atomic level and partly explained the reason for the different elution orders using the different chiral columns.
journal_name
Chiralityjournal_title
Chiralityauthors
Zhao L,Xie J,Guo F,Liu Kdoi
10.1002/chir.22836subject
Has Abstractpub_date
2018-05-01 00:00:00pages
661-669issue
5eissn
0899-0042issn
1520-636Xjournal_volume
30pub_type
杂志文章相关文献
CHIRALITY文献大全abstract::Two "click" binaphthyl chiral stationary phases were synthesized and evaluated by liquid chromatography. Their structures incorporate S-(-)-1,1'-binaphthyl moiety as the chiral selector and 1,2,3-triazole ring as the spacer. These chiral stationary phases (CSPs) allowed the efficient resolution for a wide range of rac...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22039
更新日期:2012-05-01 00:00:00
abstract::Synthetic pyrethroid insecticides are chiral compounds with multiple asymmetric positions. In this study, isomers of four commonly used pyrethroids were separated at the enantiomeric level by enantioselective high-performance liquid chromatography (HPLC), and differences between enantiomers in aquatic toxicity were ch...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20122
更新日期:2005-01-01 00:00:00
abstract::Studies of xenobiotic disposition in rodents often employ experimental designs using differing routes of administration. In an effort to investigate the effects of route of administration on enantioselective disposition of xenobiotics, a chiral polychlorinated biphenyl (PCB), racemic PCB 136, was administered as a sin...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20342
更新日期:2007-01-01 00:00:00
abstract::Six secondary phosphine oxides and their tautomeric equilibria as free ligands and in the presence of an equimolar amount of the chiral dirhodium complex Rh* are described and discussed. Discrimination of enantiomers is easily possible by inspecting the (31)P NMR resonances; some (1)H and (13)C NMR resonances are usef...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.10306
更新日期:2004-01-01 00:00:00
abstract::Doping nematic liquid crystals with nonracemic chiral compounds induces a twisted nematic (cholesteric) phase. The ability of solutes to twist the nematic phase may be related to the overall shape of the chiral dopant and consequently to its absolute configuration. The cholesteric induction is therefore a powerful too...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20482
更新日期:2008-05-15 00:00:00
abstract::Immobilized Cu(OAc)(2)-bis(oxazolines) via hydrogen bonding by SBA-15 was applied to asymmetric Henry reaction, and good enantioselectivities were obtained (up to 83% ee) between 2-methoxybenzaldehyde and CH(3)NO(2) in isopropyl alcohol (iPrOH). The catalyst could be reused seven times without any obvious loss in enan...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22104
更新日期:2012-12-01 00:00:00
abstract::The first direct asymmetric synthetic preparation of trifluoro-1-(indol-3-yl)ethanols (TFIEs) is described by an enantioselective organocatalytic method from indoles and inexpensive trifluoroacetaldehyde methyl hemiacetal. The reaction is catalyzed by hydroquinine to produce TFIEs in an almost quantitative yield and w...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20982
更新日期:2011-09-01 00:00:00
abstract::Ion channels are pharmacologic receptors and as such exhibit stereoselective interactions with drugs. Ion channels are conformationally mobile transmembrane proteins existing in a number of open and closed states. Drug interactions with these different states may differ quantitatively and qualitatively. Stereoselectiv...
journal_title:Chirality
pub_type: 杂志文章,评审
doi:10.1002/(SICI)1520-636X(1996)8:1<35::AID-CHIR8>3.0
更新日期:1996-01-01 00:00:00
abstract::Ropivacaine hydrochloride monohydrate (ropivacaine) is a new local anaesthetic agent which is administered exclusively as the (-)-(S)-form. The aim of the study was to determine whether metabolic racemisation of (-)-(S)-ropivacaine occurs. This was tested in man, rat, dog, and sheep after different routes of administr...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.530070414
更新日期:1995-01-01 00:00:00
abstract::Weinreb amide 3 was synthesized using isobutyl chloroformate, carbonyldiimidazole, or ethylcarbodiimide as the coupling agent in the reaction of Boc-phenylalanine with O,N-dimethylhydroxylamine hydrochloride. An optically active oil was isolated along with an optically inactive solid irrespective of the type of coupli...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/(SICI)1520-636X(2000)12:1<2::AID-CHIR2>3.0
更新日期:2000-01-01 00:00:00
abstract::The present study describes the development of two approaches for the determination of the enantiopurity of both enantiomers of indatraline. Initially, a method was developed using different chiral solvating agents (CSAs) for diastereomeric discrimination regarding signal separation in (1)H nuclear magnetic resonance ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22235
更新日期:2013-12-01 00:00:00
abstract::Compared to simulated moving bed (SMB) chromatography, fractional crystallization is a simple and economical method for enantioseparation. Therefore, the coupling of SMB chromatography and fractional crystallization is suggested for enantioseparation of racemic compounds. In this work, a nonsteroidal antiinflammatory ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20075
更新日期:2004-10-01 00:00:00
abstract::The aim of our study was to synthesize vinylic and pyrido-fused pyridazines with a spirano moiety and to investigate their stereochemistry by spectroscopic and HPLC analyses. The vinylic compounds 5 were obtained by Knoevenagel condensation of cyclohexylidene malonates 1 with pyridazinecarbaldehyde 2. Compound 5b exhi...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.10096
更新日期:2002-05-15 00:00:00
abstract::C2 -symmetric N,N-bis(phosphinomethyl)amines were prepared by the thermal reaction of aromatic aldehydes with ammonia and hypophosphorus acid as previously described. Both enantiomers of C2 -symmetric N,N-bis(phosphinomethyl)amine were obtained in a high enantiomeric purity through the diastereomeric salt formation wi...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22391
更新日期:2015-01-01 00:00:00
abstract::E-6087 is a nonsteroidal anti-inflammatory compound that selectively inhibits cyclooxygenase-2. Because E-6087 has a chiral center, this compound is a racemic mixture of two stereoisomers, (+)-(R)-E-6087 (E-6231) and (-)-(S)-E-6087 (E-6232). A normal-phase liquid-chromatographic method for the enantioselective determi...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20030
更新日期:2004-05-15 00:00:00
abstract::Polymorphonuclear neutrophils (PMNs) are short-lived leukocytes that die by apoptosis. Although PMNs are crucial in the defense against infection, they have been implicated in the pathogenesis of tissue injury observed in inflammatory diseases. The induction or prevention of PMN apoptosis is currently discussed as a k...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20516
更新日期:2008-02-01 00:00:00
abstract::A three-dimensional molecularly imprinted overoxidized polypyrrole/MnO2 /carbon felt (MIOPPy/MnO2 /CF) composites were fabricated, which results in increased active area of the surface of the molecularly imprinted polymers film and greatly improved electrochemical chiral recognition effect for tryptophan isomers. The ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.23126
更新日期:2019-11-01 00:00:00
abstract::Chiral sulfoxides/N-oxides (R)-1 and (R,R)-2 are effective chiral promoters in the enantioselective allylation of α-keto ester N-benzoylhydrazone derivatives 3a-g to generate the corresponding N-benzoylhydrazine derivatives 4a-g, with enantiomeric excesses as high as 98%. Representative hydrazine derivatives 4a-b were...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22159
更新日期:2013-09-01 00:00:00
abstract::Previously, a diazaphospholidine has been synthesized and evaluated as a chiral derivatizing reagent for the determination of the optical purity of chiral alcohols via 31P NMR spectroscopy (Alexakis et al., J. Org. Chem. 57:1224-1237, 1992). Our laboratory is interested in the advantageous and practical applications o...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.530060306
更新日期:1994-01-01 00:00:00
abstract::Diamino carboxylic acids have recently come to the attention of scientists working in the field of early life and its development. These are the monomers of a hypothetic early form of genetic material, the so-called Peptide Nucleic Acid (PNA) (Nielson et al., Proc Natl Acad Sci USA 2000;97:3868-3871). Since all biopol...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20422
更新日期:2007-07-01 00:00:00
abstract::Chiral discrimination in a racemic mixture of dipalmitoylphosphatidylcholine (DPPC) is induced by a new selector at the water-air interface: L-DPPC is segregated in the condensed phase of a Langmuir monolayer upon interactions with an enantiopure amphiphilic compound. ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22508
更新日期:2015-11-01 00:00:00
abstract::The impact of crystalline forces on the solid-state circular dichroism (CD) spectrum of hypothemycin (), a biologically active molecule extracted from natural sources, has been analyzed by means of time-dependent density functional theory CD calculations. Input structures were extracted from the X-ray geometry of and ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22008
更新日期:2012-09-01 00:00:00
abstract::The new linear polyesters, W1278-A, B, and C, were isolated from culture extracts of a freshwater Ascomycete fungus. Their structures were elucidated on the basis of spectroscopic analyses and chemical transformations, with the absolute configuration established by the circular dichroism (CD) method using (R)-(-)-6-hy...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20105
更新日期:2005-01-01 00:00:00
abstract::1alpha,25-Dihydroxyvitamin D(3) (1alpha,25(OH)2D3) has been shown to modulate not only proliferation and differentiation, but also apoptosis in malignant cells, indicating that it could be useful for the treatment of cancer and psoriasis. However, little information has been available on the binding conformation of th...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.1046
更新日期:2001-07-01 00:00:00
abstract::N-formylphenylalanine was subjected to optical resolution using a chiral agent such as phenylethylamine enantiomer, (R)-phenylglycine methyl ester, (S)-N-benzyl-2-aminobutanol, alone or in a mixture with each other or in a mixture with benzylamine. ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20330
更新日期:2007-01-01 00:00:00
abstract::The improvement of the biocatalytic reduction of 2-allyl-carboethoxy-cyclopentanone (2) to the corresponding cyclopentanol derivative (+)-(1R,2R)-(1) was accomplished employing baker's yeast in organic media. This chiral cyclopentanol derivative (1), analyzed by high resolution gas chromatography performed over beta-c...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/(SICI)1520-636X(1997)9:4<321::AID-CHIR1>3.
更新日期:1997-01-01 00:00:00
abstract::A summary of selected NMR studies of enantiodiscrimination phenomena regarding the use of quinine-based chiral solvating agents (CSAs) for the determination of the enantiomeric compositions in solution is reported, with explanations of their multireceptorial character offered. ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20134
更新日期:2005-01-01 00:00:00
abstract::The aim of this work was to establish structure-reactivity relationships between chiral aggregates (micelles, vesicles, and "pseudo-micelles" of amphiphilic dendrimers) and asymmetric induction. In water, micelles or vesicles formed with sugar-headed surfactants gave less than 10% ee in the reduction of prochiral keto...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/1520-636X(2001)13:1<24::AID-CHIR5>3.0.CO;2
更新日期:2001-01-01 00:00:00
abstract::Hornet silks adopt a variety of morphology such as fibers, sponge, films, and gels depending on the preparation methods. We have studied the conformation change of hornet silk proteins (Vespa mandarina) as regenerated films, using chiroptical spectrophotometer universal chiroptical spectrophotometer 1, which can measu...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22824
更新日期:2018-05-01 00:00:00
abstract::The stereochemistry of tolperisone, a chiral aryl-alkyl basic ketone was investigated by means of circular dichroism (CD) and ultraviolet (UV) spectroscopy. The unusually high optical activity of tolperisone hydrochloride in the n-->pi* region is interpreted by the presence of a chiral conformer in solution. For stere...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/1520-636X(2000)12:10<720::AID-CHIR4>3.0.CO
更新日期:2000-11-01 00:00:00