Chiral discrimination by albumin: a mechanistic study of liquid chromatographic optical resolution of nonaromatic carboxylic acids.


:In order to get further insight into the mechanism by which bovine serum albumin (BSA) discriminates between enantiomers of organic acids, some radioisotopically labeled, nonaromatic carboxylic acids were studied under varying mobile phase conditions. It was found for a series of N-alkanoyl-DL-[3H]leucines that the D-enantiomers were much more strongly retained and that the composition of the mobile phase could be adjusted to give very large (alpha > 20) enantiomeric separation factors. The elution order was consistent with what has been found earlier for other N-acyl derivatives as well as for N-arylcarbomoyl derivatives of simple aliphatic amino acids. A marked increase in the hydrophobic interaction of the D-enantiomers with the chiral phase was found upon a lowering of the mobile phase strength, conditions under which the L-form was only slightly influenced. These and other results are consistent with a chiral recognition model by which inclusion of the compound in a hydrophobic chiral cavity of BSA with simultaneous charge interaction is assumed to take place and whereby discrimination is determined by the steric bulk and orientation of the alpha-substituent.






Allenmark S




Has Abstract


1993-01-01 00:00:00












  • Synthesis of molecularly imprinted polymers using a functionalized initiator for chiral-selective recognition of propranolol.

    abstract::We present a new concept of synthesis for preparation of molecularly imprinted polymers using a functionalized initiator to replace the traditional functional monomer. Using propranolol as a model template, a carboxyl-functionalized radical initiator was demonstrated to lead to high-selectivity polymer particles prepa...


    pub_type: 杂志文章


    authors: Liu W,Holdsworth C,Ye L

    更新日期:2020-03-01 00:00:00

  • Claisen-Schmidt condensation: Synthesis of (1S,6R)/(1R,6S)-2-oxo-N,4,6-triarylcyclohex-3-enecarboxamide derivatives with different substituents in H2 O/EtOH.

    abstract::A simple, green, and direct three-component condensation of acetophenone, aromatic aldehydes with 3-oxo-N-phenylbutanamide (acetoacetanilide) to generate some novel (1S,6R)/(1R,6S)-2-oxo-N,4,6-triarylcyclohex-3-enecarboxamide derivatives was carried out over K2 CO3 (10 mol%) with high efficiency in water/ethanol as gr...


    pub_type: 杂志文章


    authors: Mousavi SR

    更新日期:2016-11-01 00:00:00

  • Influence of endotoxin on the stereoselective pharmacokinetics of oxprenolol, propranolol, and verapamil in the rat.

    abstract::The influence of endotoxin-induced inflammation on the enantioselective pharmacokinetics of propranolol, oxprenolol, and verapamil, which bind to alpha 1-acid glycoprotein, was studied in the rat. The racemic mixtures were given orally. In the control animals, for propranolol and oxprenolol, the plasma concentrations ...


    pub_type: 杂志文章


    authors: Laethem ME,Belpaire FM,Wijnant P,Rosseel MT,Bogaert MG

    更新日期:1994-01-01 00:00:00

  • Synthesis of a new enantiomerically pure P-chiral phosphine and its use in probing the mechanism of the Mitsunobu reaction.

    abstract::A new enantiomerically pure P-chiral phosphine, (S)-cyclohexylmethyl- (1-naphthyl)phosphine (1) was prepared by phosphine-borane methodology and used in a mechanistic study of the Mitsunobu reaction. Enantiomerically enriched (S)-cyclo- hexylmethyl(1-naphtyl)phosphine oxide (8) is obtained if the reaction proceeds thr...


    pub_type: 杂志文章


    authors: Watanabe T,Gridnev ID,Imamoto T

    更新日期:2000-06-01 00:00:00

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

    abstract::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) u...


    pub_type: 杂志文章


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

    更新日期:2015-05-01 00:00:00

  • Chiral doping of nematic phases and its application to the determination of absolute configuration.

    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...


    pub_type: 杂志文章


    authors: Pieraccini S,Ferrarini A,Spada GP

    更新日期:2008-05-15 00:00:00

  • Chiral memory: induction, amplification, and switching in porphyrin assemblies.

    abstract::The interaction between the tetra-anionic porphyrin H2TPPS and its copper derivative, CuTPPS, with the tetra-cationic porphyrin H2T4 and its copper derivative, CuT4, leads, in aqueous solution, to the formation of remarkably stable and kinetically inert heteroaggregates. The aggregation process is under hierarchic con...


    pub_type: 杂志文章


    authors: Rosaria L,D'urso A,Mammana A,Purrello R

    更新日期:2008-03-01 00:00:00

  • Enantioselective degradation of warfarin in soils.

    abstract::Environmental enantioselectivity information is important to fate assessment of chiral contaminants. Warfarin, a rodenticide and prescription medicine, is a chiral chemical but used in racemic form. Little is known about its enantioselective behavior in the environment. In this study, enantioselective degradation of w...


    pub_type: 杂志文章


    authors: Lao W,Gan J

    更新日期:2012-01-01 00:00:00

  • First molecules, biological chirality, origin(s) of life.

    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 ...


    pub_type: 评论,杂志文章


    authors: Caglioti L,Micskei K,Pályi G

    更新日期:2011-01-01 00:00:00

  • Nonhanded chirality in octahedral metal complexes.

    abstract::Chiral molecules can either be handed (i.e., "shoes") or nonhanded ("potatoes"). The only chiral ligand partition for tetrahedral metal complexes (or for a tetrahedral carbon atom such as that found in amino acids and other chiral biological molecules) is the fully unsymmetrical degree 6 partition (1(4)), which leads ...


    pub_type: 杂志文章


    authors: King RB

    更新日期:2001-08-01 00:00:00

  • Chiral 1,1'-binaphthyl-2,2'-dithiol-stabilized gold clusters: size separation and optical activity in the UV-vis.

    abstract::Gold particles covered with 1,1'-binaphthyl-2,2'-dithiol (BINAS) were prepared. Using size exclusion chromatography, it was possible for the first time to separate the sample into fractions with different sizes and colors. Transmission electron microscopy shows that the particles are very small, in the order of 1 nm o...


    pub_type: 杂志文章


    authors: Gautier C,Taras R,Gladiali S,Bürgi T

    更新日期:2008-03-01 00:00:00

  • Enantioselective analysis of N-hydroxymexiletine glucuronide in human plasma for pharmacokinetic studies.

    abstract::Enzymatic hydrolysis with beta-glucuronidase/sulfatase was used for the enantioselective determination of N-hydroxymexiletine glucuronide in plasma for pharmacokinetic studies. N-Hydroxymexiletine glucuronide was determined as the quantity of mexiletine released by hydrolysis (difference between the enantiomeric conce...


    pub_type: 杂志文章


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

    更新日期:1999-01-01 00:00:00

  • Enantioselective and diastereoselective Michael addition of ketone/aldehyde to trans-nitroolefins catalyzed by a novel chiral pyrrolidine-thiourea.

    abstract::The direct Michael addition reaction of cyclohexanone/aliphatic aldehydes with nitroolefins, catalyzed by a novel chiral pyrrolidine-thiourea catalyst 1a, is described. The desired 1,4-adducts were obtained in moderate yields with enantioselectivities up to 99% ee and dr up to 99:1 of the syn product. ...


    pub_type: 杂志文章


    authors: Shen Z,Zhang Y,Jiao C,Li B,Ding J,Zhang Y

    更新日期:2007-05-05 00:00:00

  • Conformational and Chiral Properties of Cyclic-tri(N-methyl-meta-benzamide) Bearing Amidino Groups.

    abstract::Cyclic triamides bearing amidino groups at the meta position of the phenyl rings were synthesized, and their conformational properties in the crystal and in solution were examined. Compound exists as a capsule-type dimer of the enantiomers with a bowl-shaped syn conformation in the crystal state. Compound exists mainl...


    pub_type: 杂志文章


    authors: Nishiyama S,Urushibara K,Masu H,Azumaya I,Kagechika H,Tanatani A

    更新日期:2015-08-01 00:00:00

  • Investigation of the chiral recognition ability of human carboxylesterase 1 using indomethacin esters.

    abstract::Human carboxylesterase 1 (hCES1) is an enzyme that plays an important role in hydrolysis of pharmaceuticals in the human liver. In this study, elucidation of the chiral recognition ability of hCES1 was attempted using indomethacin esters in which various chiral alcohols were introduced. Indomethacin was condensed with...


    pub_type: 杂志文章


    authors: Takahashi M,Takani D,Haba M,Hosokawa M

    更新日期:2020-01-01 00:00:00

  • Evaluation of the enantiomeric composition of amino acids in tobacco.

    abstract::Despite the fact that several studies have reported the concentrations of various free amino acids in tobacco, their enantiomeric composition is unknown. Both the absolute and enantiomeric compositions of proline, alanine, asparagine, aspartic acid, valine, methionine, leucine,and phenylalanine were determined for thr...


    pub_type: 杂志文章


    authors: Kullman JP,Chen X,Armstrong DW

    更新日期:1999-01-01 00:00:00

  • Two-dimensional separation of [7]helicene enantiomers on Cu(111).

    abstract::The adsorption of heptahelicene, a helically shaped polyaromatic hydrocarbon (C(30)H(18)), on a Cu(111) surface was studied by means of thermal desorption mass spectrometry (TDMS) and low energy electron diffraction (LEED) at temperatures between 130-1,000 K under ultrahigh vacuum (UHV) conditions. The molecule in the...


    pub_type: 杂志文章


    authors: Ernst KH,Kuster Y,Fasel R,Müller M,Ellerbeck U

    更新日期:2001-01-01 00:00:00

  • Evaluation of the chiral recognition properties and the column performances of three chiral stationary phases based on cellulose for the enantioseparation of six dihydropyridines by high-performance liquid chromatography.

    abstract::Separations of six dihydropyridine enantiomers on three commercially available cellulose-based chiral stationary phases (Chiralcel OD-RH, Chiralpak IB, and Chiralpak IC) were evaluated with high-performance liquid chromatography (HPLC). The best enantioseparation of the six chiral drugs was obtained with a Chiralpak I...


    pub_type: 杂志文章


    authors: Yu J,Tang J,Yuan X,Guo X,Zhao L

    更新日期:2017-03-01 00:00:00

  • Evaluation of "click" binaphthyl chiral stationary phases by liquid chromatography.

    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...


    pub_type: 杂志文章


    authors: Yu H,Yin C,Jia C,Jin Y,Ke Y,Liang X

    更新日期:2012-05-01 00:00:00

  • Resolution of enantiomers of novel C2 -symmetric aminobisphosphinic acids via diastereomeric salt formation with quinine.

    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...


    pub_type: 杂志文章


    authors: Kaboudin B,Faghihi MR,Kazemi F,Yokomatsu T

    更新日期:2015-01-01 00:00:00

  • Synthesis and characterization of conformationally rigid chiral pyridine-N-heterocyclic carbene-based palladacycles with an unexpected Pd-N bond cleavage.

    abstract::The versatility of a previously developed method for the synthesis of chiral carbene-based palladacycles is demonstrated through the synthesis of two new chiral pyridine-functionalized N-heterocyclic carbene palladacycles with different wingtip groups. The efficiency in their resolution with different counter anions a...


    pub_type: 杂志文章


    authors: Ng KH,Li Y,Tan WX,Chiang M,Pullarkat SA

    更新日期:2013-03-01 00:00:00

  • On the physical basis of asymmetry and homochirality.

    abstract::Mirror symmetry breaking is ubiquitous in our visible universe taking place in elementary particles, atoms, and molecules. Molecular chirality is not biogenic in itself, although its detection is often considered a biosignature, a conjecture inferred from the fact that we do not know life devoid of homochirality. The ...


    pub_type: 杂志文章


    authors: Cintas P,Viedma C

    更新日期:2012-11-01 00:00:00

  • Theoretical and Molecular Docking Study of Ketoconazole on Heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin as Chiral Selector.

    abstract::A molecular docking study, using molecular mechanics calculations with AutoDock and semi-empirical PM3 calculations, was used to predict the enantiodiscrimination of heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin (TMβCD) and ketoconazole (KTZ) enantiomers. A Density Functional Theory (DFT) single-point calculation at the...


    pub_type: 杂志文章


    authors: Arsad SR,Maarof H,Wan Ibrahim WA,Aboul-Enein HY

    更新日期:2016-03-01 00:00:00

  • Chemoenzymatic and microbial dynamic kinetic resolutions.

    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...


    pub_type: 杂志文章


    authors: Kamaruddin AH,Uzir MH,Aboul-Enein HY,Halim HN

    更新日期:2009-04-01 00:00:00

  • Ion channels as pharmacologic receptors: the chirality of drug interactions.

    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...


    pub_type: 杂志文章,评审


    authors: Triggle DJ

    更新日期:1996-01-01 00:00:00

  • Surface-enhanced chiroptical spectroscopy with superchiral surface waves.

    abstract::We study the chiroptical properties of one-dimensional photonic crystals supporting superchiral surface waves by introducing a simple formalism based on the Fresnel reflection matrix. We show that the proposed framework provides useful insights on the behavior of all the relevant chiroptical quantities, allowing for a...


    pub_type: 杂志文章


    authors: Pellegrini G,Finazzi M,Celebrano M,Duò L,Biagioni P

    更新日期:2018-07-01 00:00:00

  • Synthesis and stereochemistry of dispiro substituted pyridazines: application of ellipticity-absorbance ratio spectra for proving enantiomeric relationship by HPLC-CD/UV detection.

    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...


    pub_type: 杂志文章


    authors: Beke G,Gergely A,Szász G,Szentesi A,Nyitray J,Barabás O,Harmath V,Mátyus P

    更新日期:2002-05-15 00:00:00

  • Programmed assembly of rigid-rod beta-barrel pores: thermal inversion of chirality.

    abstract::The programmed assembly of p-octiphenyl rods carrying six complementary tripeptide strands was studied in the presence of bilayer membranes using circular dichroism (CD) spectroscopy. Thermal CD experiments demonstrated programmed assembly of anionic and cationic rods into supramolecules at low temperature that irreve...


    pub_type: 杂志文章


    authors: Sakai N,Matile S

    更新日期:2004-01-01 00:00:00

  • Gas chromatographic separation of saturated aliphatic hydrocarbon enantiomers on permethylated beta-cyclodextrin.

    abstract::Enantiomers of chiral aliphatic hydrocarbons are generally difficult to separate because they lack functional groups to be derivatized in order to generate diastereomers. The systematic and quantitative separation of a series of branched hydrocarbon enantiomers using a chiral cyclodextrin stationary phase and a cryost...


    pub_type: 杂志文章


    authors: Meierhenrich UJ,Nguyen MJ,Barbier B,Brack A,Thiemann WH

    更新日期:2003-01-01 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