Screening Approach for Chiral Separation of β-Aminoketones by HPLC on Various Polysaccharide-Based Chiral Stationary Phases.


:Nine β-aminoketones were synthesized via Mannich reaction when benzaldehyde was condensed with some primary amines and acetophenone. The purified compounds were identified by using spectroscopic methods. The enantiomeric separation of these derivatives was carried out by high-performance liquid chromatography (HPLC) using several coated and immobilized polysaccharide stationary phases, namely, Chiralcel(®) OD-H, Chiralcel(®) OD, Chiralcel(®) OJ, Chiralpak(®) AD, Chiralpak(®) IA, and Chiralpak(®) IB using different mobile phases composed of n-hexane and alcohol mixed in various ratios or pure ethanol or isopropanol. The retention behavior and selectivity of these chiral stationary phases were examined in isocratic normal phase mode. The results indicate that cellulose derivatives have higher enantioselectivity than amylose derivatives for the separation of racemic β-amino ketones.






Addadi K,Sekkoum K,Belboukhari N,Cheriti A,Aboul-Enein HY




Has Abstract


2015-05-01 00:00:00












  • Chemoselectivity issues of the asymmetric interaction between cyclohexanone, β-nitrostyrene, and benzoic acid under 5-aryl prolinate's organocatalysis.

    abstract::4-l-menthyloxycarbonyl 5-aryl prolinates were studied as organocatalysts of a novel three-component reaction of cyclohexanone, benzoic acid, and β-nitrostyrene. The presence of ortho-halogen atom in 5-aryl fragment of the catalyst is favored for driving the formation of chiral 7a-hydroxyoctahydro-2H-indol-2-one scaffo...


    pub_type: 杂志文章


    authors: Ivantcova PM,Kudryavtsev KV

    更新日期:2020-06-01 00:00:00

  • Capillary electrophoresis of herbicides. III. Evaluation of octylmaltopyranoside chiral surfactant in the enantiomeric separation of phenoxy acid herbicides.

    abstract::A chiral alkylglucoside surfactant, namely n-octyl-beta-D-maltopyranoside (OM), was evaluated in the enantiomeric separation of phenoxy acid herbicides. The enantiomeric resolution of the phenoxy acid herbicides could be manipulated readily by adjusting the surfactant concentration, ionic strength, pH, the percent org...


    pub_type: 杂志文章


    authors: Mechref Y,el Rassi Z

    更新日期:1996-01-01 00:00:00

  • Enantioselective Friedel-Crafts reaction of indoles with trifluoroacetaldehyde catalyzed by Cinchona alkaloids.

    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...


    pub_type: 杂志文章


    authors: Borkin DA,Landge SM,Török B

    更新日期:2011-09-01 00:00:00

  • Synthesis, resolution, and chiroptical properties of hemicryptophane cage controlling the chirality of propeller arrangement of a C3 triamide unit.

    abstract::The five-steps synthesis of a hemicryptophane cage combining a benzene-1,3,5-tricarboxamide unit and a cyclotriveratrylene (CTV) moiety is described. Chiral high-performance liquid chromatography (HPLC) was used to resolve the racemic mixture. The absolute configuration of the isolated enantiomers was assigned by comp...


    pub_type: 杂志文章


    authors: Long A,Jean M,Albalat M,Vanthuyne N,Giorgi M,Górecki M,Dutasta JP,Martinez A

    更新日期:2019-11-01 00:00:00

  • Asymmetric Borane Reduction of Prochiral Ketones Catalyzed By Helical Poly[(S)-3-vinyl-2,2'-dihydroxy-1,1'-binaphthyl].

    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...


    pub_type: 杂志文章


    authors: Qin G,Chen Y,Yang L,Yang N,Yang Z

    更新日期:2015-07-01 00:00:00

  • A Solid Phase Vibrational Circular Dichroism Study of Polypeptide-Surfactant Interaction.

    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...


    pub_type: 杂志文章


    authors: Novotná P,Urbanová M

    更新日期:2015-12-01 00:00:00

  • Effect of the mobile phase on the retention behavior of optical isomers of the mandelic acid derivative methyl 2-phenyl-2-(tetrahydropyranyloxy) acetate by chiral HPLC.

    abstract::Conditions for separation of enantiomers of a mandelic acid derivative, methyl 2-phenyl-2-(tetrahydropyranyloxy) acetate (the analyte) were studied. Because of the presence of two chiral carbons, the analyte consists of four stereoisomers stable at ambient temperature. Chiral HPLC of the analyte resulted in four peaks...


    pub_type: 杂志文章


    authors: Shen B,Xu X,Chen J,Zhang X,Xu B

    更新日期:2006-09-01 00:00:00

  • Enantioselectivity in the metabolism of mexiletine by conjugation in female patients with the arrhythmic form of chronic Chagas' heart disease.

    abstract::The phenomenon of enantioselectivity in the metabolism of mexiletine (MEX) conjugation was investigated in eight female patients with the arrhythmic form of chronic Chagas' heart disease treated with racemic mexiletine hydrochloride (two 100 mg capsules every 8 hr). Blood samples were collected up to 24 hr after the a...


    pub_type: 临床试验,杂志文章


    authors: Lanchote VL,Cesarino EJ,Santos VJ,Mere Júnior Y,Santos SR

    更新日期:1999-01-01 00:00:00

  • Unexpected rearrangement of enantiomerically pure 3-aminoquinuclidine as a simple way of preparing diastereomeric octahydropyrrolo[2,3-c]pyridine derivatives.

    abstract::Reaction of (S)- or (R)-3-aminoquinuclidine with 2-chloropyrimidine or 2-bromopyrimidine led to an unexpected formation of both cis- and trans-octahydropyrrolo [2,3]pyridine derivatives. A single-step synthesis of two of the four stereoisomers of these octahydropyrrolo[2,3]pyridine derivatives provides a convenient wa...


    pub_type: 杂志文章


    authors: Goljer I,Molinari A,He Y,Nogle L,Sun W,Campbell B,McConnell O

    更新日期:2009-07-01 00:00:00

  • Enantiomeric resolution and modeling of DL-alanine-DL-tryptophan dipeptide on amylose stationary phase.

    abstract::The enantiomeric resolution of DL-alanine-DL-tryptophan dipeptide is described on amylose stationary phase. The eluent used was CH3 OH─CH3 COONH4 (10mM)─CH3 CN (50: 40, 10) at 0.8-mL/min flow, 230-nm detection, 25-minute run time, and 25°C ± 1°C temperature. The chiral phase was amylose [AmyCoat RP (15 cm × 0.46 cm × ...


    pub_type: 杂志文章


    authors: Ali I,Khattab RA,Alothman ZA,Badjah AY,Alwarthan A

    更新日期:2018-04-01 00:00:00

  • Enantioselective photoreaction of achiral tropolone ether in inclusion crystals with optically active host compounds.

    abstract::Achiral 4-isopropyltropolone methyl ether (3) included in an optically active host compound (-)-1 yielded optically active photocyclization products (-)-5 and (-)-6 in 96 and 90% ee, respectively, upon photoirradiation in the solid state. ...


    pub_type: 杂志文章


    authors: Tanaka K,Nagahiro R,Urbanczyk-Lipkowska Z

    更新日期:2002-07-01 00:00:00

  • Chiral discrimination of the analgesic cizolirtine by using cyclodextrins: A (1)H NMR study on the solution structures of their host-guest complexes.

    abstract::The use of four cyclodextrins (three native and one beta-CD derivative) as NMR chiral solvating agents to resolve the enantiomers of (+/-)-cizolirtine, 1, and its chemical precursor (the carbinol, (+/-)-2), was investigated. The best enantiodiscrimination occurred when beta-cyclodextrin was used. ROESY experiments wer...


    pub_type: 杂志文章


    authors: Redondo J,Blázquez MA,Torrens A

    更新日期:1999-01-01 00:00:00

  • A stereodynamic fluorescent probe for amino acids. Circular dichroism and circularly polarized luminescence analysis.

    abstract::The use of stereodynamic probes is becoming one of the leading strategies for the fast and effective determination of enantiomeric excess. Recently, we reported a series of novel molecular architectures based on a modified tris(2-pyridylmethyl)amine complex (TPMA), which are able to amplify the electronic CD, in the c...


    pub_type: 杂志文章


    authors: Carmo Dos Santos NA,Badetti E,Licini G,Abbate S,Longhi G,Zonta C

    更新日期:2018-01-01 00:00:00

  • Circular dichroism and the interactions of water soluble porphyrins with DNA.

    abstract::The size, sign, and profile of induced circular dichroism (CD) features in the Soret region are reliable indicators of the binding modes of porphyrins and metalloporphyrins to DNA. Porphyrins shown (using such CD criteria) to be intercalators in monodispersed DNA duplexes prove extremely useful for the detection and c...


    pub_type: 杂志文章,评审


    authors: Pasternack RF

    更新日期:2003-05-05 00:00:00

  • Isolation and identification of sapotexanthin 5,6-epoxide and 5,8-epoxide from red mamey (Pouteria sapota).

    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...


    pub_type: 杂志文章


    authors: Murillo E,Agócs A,Nagy V,Király SB,Kurtán T,Toribio EM,Lakey-Beitia J,Deli J

    更新日期:2020-05-01 00:00:00

  • Normal phase chiral HPLC of methylphenidate: comparison of different polysaccharide-based chiral stationary phases.

    abstract::A comparison of the enantiomeric resolution of (+/-)-threo-methylphenidate (MPH) (Ritalin) was achieved on different polysaccharide based chiral stationary phases. The mobile phase used was hexane-ethanol-methanol-trifluoroacetic acid (480:9.75:9.75:0.5, v/v/v/v). Benzoic acid and phenol were used as the mobile phase ...


    pub_type: 杂志文章


    authors: Aboul-Enein HY,Ali I

    更新日期:2002-01-01 00:00:00

  • Excitatory amino acid receptor antagonists: resolution, absolute stereochemistry, and pharmacology of (S)- and (R)-2-amino-2-(5-tert-butyl-3-hydroxyisoxazol-4-yl)acetic acid (ATAA).

    abstract::We have previously shown that (RS)-2-amino-2-(5-tert-butyl-3-hydroxyisoxazol-4-yl)acetic acid (ATAA) is an antagonist at N-methyl-D-aspartic acid (NMDA) and (RS)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid (AMPA) receptors. We have now resolved ATAA via diastereomeric salt formation using N-BOC protected...


    pub_type: 杂志文章


    authors: Johansen TN,Frydenvang K,Ebert B,Madsen U,Krogsgaard-Larsen P

    更新日期:1997-01-01 00:00:00

  • Three-Dimensional Chemical Structure Search Using the Conformational Code for Organic Molecules (CCOM) Program.

    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...


    pub_type: 杂志文章


    authors: Izumi H,Nafie LA,Dukor RK

    更新日期:2016-05-01 00:00:00

  • Heparin-induced circular dichroism of an achiral, bicyclic species.

    abstract::Antimalarial drugs have shown potential in suppressing the role of glycosaminoglycans (GAGs) in the pathology of prion protein conformational disorders (e.g. "Mad Cow" disease) by competing for sites of electrostatic interaction. In this study, circular dichroism (CD) and UV/Visible (UV/Vis) absorption spectroscopy te...


    pub_type: 杂志文章


    authors: Stanley FE,Warner AM,McWilliams KM,Stalcup AM

    更新日期:2011-01-01 00:00:00

  • Time-resolved circular dichroism in carbonmonoxy-myoglobin: the central role of the proximal histidine.

    abstract::A calculation of the circular dichroism (CD) spectra of carbonmonoxy- and deoxy-myoglobin is carried out in relation to a time-resolved CD experiment. This calculation allows us to assign a dominant role to the proximal histidine in the definition of the electronic normal modes and to interpret the transient CD struct...


    pub_type: 杂志文章


    authors: Dartigalongue T,Hache F

    更新日期:2006-05-05 00:00:00

  • Time-resolved circularly polarized luminescence of Eu3+ -based systems.

    abstract::Chiral Eu3+ -based systems are frequently studied via circularly polarized luminescence spectroscopy. The emission lifetimes of each circular polarization, however, are virtually always ignored, because in a homogeneous sample of emitters, there should be no difference between the two. However, we show that in less ro...


    pub_type: 杂志文章


    authors: Hananel U,Schwartz G,Paiss G,Arrico L,Zinna F,Di Bari L,Cheshnovsky O,Markovich G

    更新日期:2020-12-30 00:00:00

  • Conformation change of hornet silk proteins in the solid phase in response to external stimulation.

    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...


    pub_type: 杂志文章


    authors: Kuroda R,Kameda T

    更新日期:2018-05-01 00:00:00

  • Chiroptical property tuning of supramolecular assemblies in polymer matrices.

    abstract::Chiroptical materials have received much attention in diverse fields for applications such as displays, sensors, smart memory devices, and catalysis. Here, we develop a simple fabrication method for polymer films with tunable chiroptical properties using small amounts of self-assembling fluorescent dye as an additive....


    pub_type: 杂志文章


    authors: Jintoku H,Ihara H

    更新日期:2020-05-01 00:00:00

  • Simultaneous Enantioseparation of Aldohexoses and Aldopentoses Derivatized With L-Tryptophanamide by Reversed Phase HPLC Using Butylboronic Acid as a Complexation Reagent of Monosaccharides.

    abstract::Three aldohexoses, glucose, galactose, and mannose, and three aldopentoses, arabinose, xylose, and ribose, were derivatized with L-tryptophanamide (L-TrpNH2 ) under alkaline conditions. Using a basic mobile phase (pH 9.2), the three aldohexoses or the three aldopentoses were simultaneously enantioseparated, respective...


    pub_type: 杂志文章


    authors: Shou M,Terashima H,Aizawa S,Taga A,Yamamoto A,Kodama S

    更新日期:2015-07-01 00:00:00

  • HPLC enantioseparation and absolute configuration of novel anti-inflammatory pyrrole derivatives.

    abstract::The assignment of the absolute configuration of novel anti-inflammatory pyrrole derivatives has been accomplished by a combined strategy based on independent physical methods. The key step of our stereochemical characterization approach is the production at mg-scale of enantiomerically pure forms by HPLC on Chiralpak ...


    pub_type: 杂志文章


    authors: Biava M,Cirilli R,Fares V,Ferretti R,Gallinella B,La Torre F,Poce G,Porretta GC,Supino S,Villani C

    更新日期:2008-06-01 00:00:00

  • Photo-ionization spectroscopy and mass spectrometry of some molecular and supramolecular asymmetric systems in the isolated state.

    abstract::Asymmetric molecular and supramolecular systems are characterized by: i. the circular dicroism in the angular distribution of valence photoelectrons emitted from randomly oriented chiral molecules by their interaction with circularly polarized VUV light; ii. the different stability and reactivity of diastereomeric agg...


    pub_type: 杂志文章


    authors: Giardini A,Paladini A,Catone D,Piccirillo S,Rondino F,Satta M,Filippi A,Speranza M,Turchini S,Zema N

    更新日期:2006-08-01 00:00:00

  • An improved synthesis of the enantiomers of BM-5 and their effects on the central in vivo release of acetylcholine.

    abstract::Racemic N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM-5), a putative postsynaptic agonist and presynaptic antagonist at muscarinic receptors, was resolved into the enantiomers by a new method suitable for large scale preparation. The method involves a chemoselective N-debenzylation as the key step. The en...


    pub_type: 杂志文章


    authors: Nilsson BM,De Boer P,Grol CJ,Hacksell U

    更新日期:1992-01-01 00:00:00

  • Enantioseparation of chiral perfluorooctane sulfonate (PFOS) by supercritical fluid chromatography (SFC): Effects of the chromatographic conditions and separation mechanism.

    abstract::Perfluorooctane sulfonate (PFOS) is one of the most frequently detected perfluoroalkyl substances in environmental and human samples. Previous studies have shown that nonracemic PFOS in biological samples can be used as a marker of PFOS exposure sources. In recent years, supercritical fluid chromatography (SFC) has em...


    pub_type: 杂志文章


    authors: Zhao L,Chen F,Guo F,Liu W,Liu K

    更新日期:2019-10-01 00:00:00

  • Chiroptical properties of cation complexes of chiral phenazino-18-crown-6 ether-type hosts.

    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...


    pub_type: 杂志文章


    authors: Szarvas S,Szalay L,Vass E,Hollósi M,Samu E,Huszthy P

    更新日期:2005-06-01 00:00:00

  • From cosmic chirality to protein structure: Lord Kelvin's legacy.

    abstract::A selection of my work on chirality is sketched in two distinct parts of this lecture. Symmetry and Chirality explains how the discrete symmetries of parity P, time reversal T, and charge conjugation C may be used to characterize the properties of chiral systems. The concepts of true chirality (time-invariant enantiom...


    pub_type: 杂志文章,评审


    authors: Barron LD

    更新日期:2012-11-01 00:00:00