Abstract:
:The separation methods of the enantiomers of two β-blockers and tryptophan were studied using capillary electrochromatography with heparin covalently as well as non-covalently, bonded onto the capillary inner wall as stationary phase and electrokinetic chromatography with heparin as pseudostationary phase. In the case of heparin, used as a stationary phase, the method was unable to resolve enantiomers in both cases β-blockers and tryptophan. On the other hand, when heparin was used as a pseudostationary phase, the resolution of the enantiomers was obtained only with 3-aminopropyltriethoxysilane which were immobilised onto the inner phase of the capillary. The results of this study let us infer that the electrostatic, hydrophobic, and steric interactions were involved in the separation mechanisms. The separation was achieved in less than 10 minutes under the optimized conditions: 30 mM phosphate buffer (pH 2.5) with the adding of 15 mg/mL of heparin at 15°C and 10 kV. The usefulness of heparin as a chiral selector both in electrokinetic chromatography using 3-aminopropyltriethoxysilane attached to the capillary was demonstrated for the first time. The developed method was powerful, sensitive, and fast, and it could be considered an important alternative to conventional methods used for chiral separation.
journal_name
Chiralityjournal_title
Chiralityauthors
Liu Y,Sombra LL,Stege PWdoi
10.1002/chir.22972subject
Has Abstractpub_date
2018-06-25 00:00:00eissn
0899-0042issn
1520-636Xpub_type
杂志文章相关文献
CHIRALITY文献大全abstract::Several biologically active compounds structurally include the enantiopure 2-substituted-1,4-benzodioxane scaffold. The straightforward racemization that affects reactions involving most of the common chemical reactives is thus a crucial issue. The developing of a completely stereo-controlled synthetic route that does...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22968
更新日期:2018-07-01 00:00:00
abstract::The macrocyclic glycopeptide, ristocetin A, was covalently bonded to a silica gel support and evaluated as a liquid chromatographic (LC) chiral stationary phase (CSP). Over 230 racemates were resolved in either the reversed-phase mode, the normal-phase mode, or the polar-organic mode. The retention behavior and select...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/(SICI)1520-636X(1998)10:5<434::AID-CHIR10>
更新日期:1998-01-01 00:00:00
abstract::Plasmonic nanoparticles (NPs) adsorbing onto helical bacteria can lead to formation of NP helicoids with micron scale pitch. Associated chiroptical effects can be utilized as bioanalytical tool for bacterial detection and better understanding of the spectral behavior of helical self-assembled structures with different...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.23225
更新日期:2020-07-01 00:00:00
abstract::Origin(s) of biological chirality appear(s) to be intimately connected to origin(s) of life. Prebiotic evolution toward these important turning points can be traced back to single chiral molecules. These can be small (monomeric) units as amino acids or monosaccharides or oligomers as oligo-RNA type molecules. Earlier ...
journal_title:Chirality
pub_type: 评论,杂志文章
doi:10.1002/chir.20796
更新日期:2011-01-01 00:00:00
abstract::Two new carotenoids, sapotexanthin 5,6-epoxide and sapotexanthin 5,8-epoxide, have been isolated from the ripe fruits of red mamey (Pouteria sapota). Sapotexanthin 5,6-epoxide was also prepared by partial synthesis via epoxidation of sapotexanthin, and the (5R,6S) and (5S,6R) stereoisomers were identified by high-perf...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.23206
更新日期:2020-05-01 00:00:00
abstract::Recent discovery of asymmetric desymmetrization of meso-heterocycles using (R,R)-(salen)manganese complex 2 as a catalyst allowed easy access to optically active 2,3,4-trisubstituted pyrrolidines. Taking advantage of this new reaction, we could achieve the short-step synthesis of (-)-swainsonine 1. ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/(SICI)1520-636X(2000)12:5/6<464::AID-CHIR2
更新日期:2000-06-01 00:00:00
abstract::A series of 1,4-disubstituted piperazine derivatives with hypnotic activity were examined on three polysaccharide-based chiral stationary phases, namely, Chiracel OD, Chiracel OJ and Chiralpak AD. It was possible to resolve all the compounds on all the phases examined (1.13 = alpha = 3.54). Cellulose tris(4-methyl...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/(SICI)1520-636X(1999)11:10<790::AID-CHIR9>
更新日期:1999-01-01 00:00:00
abstract::Massarigenin A (1) and papyracillic acids A (2) and B (3) were isolated from the endophytic fungus Microsphaeropsis sp. Their structures were elucidated by multidimensional nuclear magnetic resonance spectroscopy; the structure of massarigenin A (1) was also confirmed by X-ray crystallography. The absolute configurati...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20985
更新日期:2011-09-01 00:00:00
abstract::We introduce a method to detect the activity of ion channels and pores with circular dichroism (CD) spectroscopy. G-quartets obtained by potassium templated self-assembly of 5'-guanosine monophosphate (GMP) are used as CD probes, the bee-toxin melittin as representative pore and gramicidin A as representative ion chan...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20526
更新日期:2008-09-01 00:00:00
abstract::In this computational study, we illustrate a method for computing phosphorescence and circularly polarized phosphorescence spectra of molecular systems, which takes into account vibronic effects including both Franck-Condon and Herzberg-Teller contributions. The singlet and triplet states involved in the phosphorescen...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22864
更新日期:2018-07-01 00:00:00
abstract::Herein we report CD spectroscopic studies on complexes of (R,R)-dimethyl-, (R,R)-diisobutyl-, and (S,S)-di-sec-butyl-phenazino-18-crown-6 ligands (Scheme 1) with selected alkali (Na+, K+), alkaline earth (Mg2+, Ca2+), and transition-metal (Ag+, Zn2+, Ni2+, Cd2+, Pb2+) cations. The complexation was monitored in the 300...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20162
更新日期:2005-06-01 00:00:00
abstract::An increase in both retention and enantioselectivity for some beta-blocking agents was observed when exchanging potassium to sodium ion in the buffer used as mobile phase. A large effect of ionic strength on retention was observed, while the enantioselectivity was constant. ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/(SICI)1520-636X(1998)10:6<513::AID-CHIR2>3
更新日期:1998-01-01 00:00:00
abstract::Three chiral derivatives of the alkaloid sparteine (bispidines), characterized by the 3,7-diazabicyclo[3.3.1]nonane moiety, were designed as efficient ligands in a number of enantioselective reactions due to their metal coordination properties. A full evaluation of the 3D properties of the compounds was carried out, a...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22586
更新日期:2016-04-01 00:00:00
abstract::The modern use of preparative chromatography in pharmaceutical development is illustrated by the case of a recent preclinical candidate from these laboratories. The synthesis of the candidate employed a coupling of two enantiopure intermediates, each of which could be resolved using preparative chiral chromatography. ...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20378
更新日期:2007-09-01 00:00:00
abstract::We studied the interaction of poly-l-lysine (PLL) and poly-l-arginine (PLAG) with sodium dodecyl sulfate (SDS) surfactant and the interaction of poly-l-glutamic acid (PLGA) and poly-l-aspartic acid (PLAA) with tetradecyltrimethylammonium bromide (TTAB) surfactant using vibrational circular dichroism (VCD) spectroscopy...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22534
更新日期:2015-12-01 00:00:00
abstract::A series of representative optically active derivatives of 4-hydroxy-5-alkylcyclopent-2-en-1-one were prepared from the respective 2-furyl methyl carbinols via the Piancatelli rearrangement followed by the enzymatic kinetic resolution of racemates. Applicability of chiroptical methods (experimental and calculated elec...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22322
更新日期:2014-06-01 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::The application of Chiral Technology, or the (extensive) use of techniques or tools for the determination of absolute stereochemistry and the enantiomeric or chiral separation of racemic small molecule potential lead compounds, has been critical to successfully discovering and developing chiral drugs in the pharmaceut...
journal_title:Chirality
pub_type: 杂志文章,评审
doi:10.1002/chir.20399
更新日期:2007-09-01 00:00:00
abstract::Enantioselective catalytic epoxidation of olefins is an important problem from both practical and mechanistic points of view. The origins of chiral induction by asymmetric porphyrin and salen complexes were investigated by FT-NMR T1 relaxation techniques. A new chiral vaulted porphyrin (1) that carries (S)-binaphthyl-...
journal_title:Chirality
pub_type: 杂志文章
doi:
更新日期:1998-01-01 00:00:00
abstract::This review tracks a decade of dynamic kinetic resolution developments with a biocatalytic inclination using enzymatic/microbial means for the resolution part followed by the racemization reactions either by means of enzymatic or chemocatalyst. These fast developments are due to the ability of the biocatalysts to sign...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20619
更新日期:2009-04-01 00:00:00
abstract::The stereolability of chiral Hoveyda-Grubbs II type ruthenium complexes bearing N-heterocyclic carbene (NHC) ligands with Syn-phenyl groups on the backbone and Syn- or Anti-oriented o-tolyl N-substituents was studied by resorting to dynamic high-performance liquid chromatography (D-HPLC). A complete chromatographic pi...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22487
更新日期:2015-10-01 00:00:00
abstract::Racemic 1-phenylethylamine was optically resolved by its own derivative formed with glutaric acid namely (+)-(R)-N-(1-phenylethyl)glutaramic acid. The amide acid resolving agent was synthesized from (+)-(R)-1-phenylethylamine by N-derivatization. The glutaric acid derivative was the next in a homologous series of dica...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20377
更新日期:2007-03-01 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 two enantiomers of 2,2'-bioxirane were synthesized, and their chiroptical properties were thoroughly investigated in various solvents by polarimetry, vibrational circular dichroism (VCD), and Raman optical activity (ROA). Density functional theory (DFT) calculations at the B3LYP/aug-cc-pVTZ level revealed the pres...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22814
更新日期:2018-04-01 00:00:00
abstract::Searching the 3D structural fragments of organic molecules is challenging because of structural differences between X-ray and theoretically calculated geometries and the conformational flexibility of substituents. The codification program called Conformational Code for Organic Molecules (CCOM) can be used to unambiguo...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22596
更新日期:2016-05-01 00:00:00
abstract::The optically active mixed-ligand fac(S)-tris(thiolato)rhodium(III) complexes, ΔL -fac(S)-[Rh(aet)2 (L-cys-N,S)](-) (aet = 2-aminoethanethiolate, L-cys = L-cysteinate) () and ΔLL -fac(S)-[Rh(aet)(L-cys-N,S)2 ](2-) were newly prepared by the equatorial preference of the carboxyl group in the coordinated L-cys ligand. T...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22546
更新日期:2016-01-01 00:00:00
abstract::The application of helical poly[(S)-3-vinyl-2,2'-dihydroxy-1, 1'-binaphthyl] (L*) in the asymmetric borane reduction of prochiral ketones was studied. The results showed that L* had excellent catalytic activity as well as enantioselectivity, giving up to 96% yield and up to 99% enantiomeric excess (ee) of the correspo...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.22459
更新日期:2015-07-01 00:00:00
abstract::The attempts of applying chiroptical spectroscopy to supramolecular chirality are reviewed with a focus on vibrational circular dichroism (VCD). Examples were taken from gels, solids, and monolayers formed by low-molecular mass weight chiral gelators. Particular attention was paid to a group of gelators with perfluoro...
journal_title:Chirality
pub_type: 杂志文章,评审
doi:10.1002/chir.22482
更新日期:2015-10-01 00:00:00
abstract::Compound A, a novel disubstituted pyrrolidine acid, is a member of a new class of agents that are potentially useful for the treatment of diabetes and dyslipidemia. The absolute configuration of this compound was determined by using vibrational circular dichroism (VCD). The results are in agreement with the assignment...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/chir.20316
更新日期:2006-09-01 00:00:00
abstract::rac-Isradipine is a dihydropyridine type calcium antagonist. Its calcium entry blocking effect is due primarily to the (+)-(S)-enantiomer. This study describes a sensitive enantioselective method for the determination of isradipine in human serum. Following alkaline extraction into hexane, the enantiomers of isradipin...
journal_title:Chirality
pub_type: 杂志文章
doi:10.1002/(SICI)1520-636X(1998)10:9<808::AID-CHIR6>3
更新日期:1998-01-01 00:00:00