Separation of amino acid enantiomers by micelle-enhanced ultrafiltration.

Abstract:

:A Micelle-enhanced ultrafiltration (MEUF) separation process was investigated that can potentially be used for large-scale enantioseparations. Copper(II)-amino acid derivatives dissolved in nonionic surfactant micelles were used as chiral selectors for the separation of dilute racemic amino acids solutions. For the alpha-amino acids phenylalanine, phenylglycine, O-methyltyrosine, isoleucine, and leucine good separation was obtained using cholesteryl L-glutamate and Cu(II) ions as chiral selector with an operational enantioselectivity (alpha(op)) up to 14.5 for phenylglycine. From a wide set of substrates, including four beta-amino acids, it was concluded that the performance of this system is determined by two factors: the hydrophobicity of the racemic amino acid, which results in a partitioning of the racemic amino acid over micelle and aqueous solution, and the stability of the diastereomeric complex formed upon binding of the amino acid with the chiral selector. The chiral hydrophobic cholesteryl anchor of the chiral selector also plays an active role in the recognition process, since inversion of the chirality of the glutamate does not yield the reciprocal enantioselectivities. However, if the cholesteryl group is replaced by a nonchiral alkyl chain, reciprocal operational enantioselectivities are found with enantiomeric glutamate selectors.

journal_name

Chirality

journal_title

Chirality

authors

De Bruin TJ,Marcelis AT,Zuilhof H,Rodenburg LM,Niederländer HA,Koudijs A,Overdevest PE,Van der Padt A,Sudhölter EJ

doi

10.1002/1520-636X(2000)12:8<627::AID-CHIR5>3.0.CO;

subject

Has Abstract

pub_date

2000-08-01 00:00:00

pages

627-36

issue

8

eissn

0899-0042

issn

1520-636X

pii

10.1002/1520-636X(2000)12:8<627::AID-CHIR5>3.0.CO;

journal_volume

12

pub_type

杂志文章
  • Enantiomeric separation and simulation studies of pheniramine, oxybutynin, cetirizine, and brinzolamide chiral drugs on amylose-based columns.

    abstract::Solid phase extraction (SPE)-chiral separation of the important drugs pheniramine, oxybutynin, cetirizine, and brinzolamide was achieved on the C18 cartridge and AmyCoat (150 x 46 mm) and Chiralpak AD (25 cm x 0.46 cm id) chiral columns in human plasma. Pheniramine, oxybutynin, cetirizine, and brinzolamide were resolv...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22276

    authors: Ali I,Al-Othman ZA,Al-Warthan A,Alam SD,Farooqi JA

    更新日期:2014-03-01 00:00:00

  • Comparative study on kynurenic acid production in the rat striatum by tryptophan enantiomers: an in vivo microdialysis study.

    abstract::Kynurenic acid (KYNA), an endogenous antagonist of N-methyl-D-aspartate and α(7) nicotinic acetylcholine receptors, is one of the L-tryptophan (Trp) metabolites. To compare the level of KYNA produced in the striatum of rats after independent administration of L-Trp and D-Trp, rats were intraperitoneally administered L...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20938

    authors: Ishii K,Iizuka H,Ogaya T,Song Z,Fukushima T

    更新日期:2011-01-01 00:00:00

  • Chiral high-performance liquid chromatographic analysis of antifungal SCH 56592 and evaluation of its chiral inversion in animals and humans.

    abstract::SCH 56592 is a novel triazole antifungal agent that is active both orally and intravenously in animal models of infection. This compound is in Phase II-III clinical trials for the treatment of systemic fungal infections. SCH 56592 is a single enantiomer with four stereogenic centers; therefore, it was necessary to eva...

    journal_title:Chirality

    pub_type: 临床试验,杂志文章

    doi:10.1002/1520-636X(2000)12:7<590::AID-CHIR7>3.0.CO;

    authors: Kim H,Lin CC,Laughlin M,Lovey R,Saksena A,Heimark L,Nomeir AA

    更新日期:2000-07-01 00:00:00

  • Investigation of the stability of Chiralpak AD chiral stationary phase under various solvent conditions and development of a method to identify stationary phase-derived polymer contamination.

    abstract::The stability of Chiralpak AD chiral stationary phase under various solvent conditions was investigated. An analytical method for the detection of the presence of solubilized Chiralpak AD coating was developed using CD spectroscopy (CD signal at 245 nm). In addition, NMR analysis of the solubilized polymer revealed a ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20348

    authors: Welch CJ,Fairchild J,Sajonz P

    更新日期:2007-08-01 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 ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22028

    authors: Cintas P,Viedma C

    更新日期:2012-11-01 00:00:00

  • Stereoselective kinetics of warfarin binding to human serum albumin: effect of an allosteric interaction.

    abstract::Kinetic and equilibrium binding studies were performed on the interaction of warfarin enantiomers with human serum albumin (HSA) in the absence and presence of lorazepam acetate (LoAc) enantiomers. Binding kinetics were followed by recording changes in the fluorescence of warfarin upon binding to HSA using the stopped...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10113

    authors: Fitos I,Visy J,Kardos J

    更新日期:2002-05-15 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 ...

    journal_title:Chirality

    pub_type: 评论,杂志文章

    doi:10.1002/chir.20796

    authors: Caglioti L,Micskei K,Pályi G

    更新日期:2011-01-01 00:00:00

  • Absolute configuration of oplopanone derivatives from Serphidium stenocephalum: ECD spectra of acyclic ketones with front-octant contributions.

    abstract::The electronic circular dichroism (ECD) spectra of two sesquiterpenoids (1 and 2) related to oplopanone, obtained from a methanolic extract of the plant Serphidium stenocephalum (Artemisia stenocephala), were measured and reproduced by means of time-dependent density functional theory (TDDFT) calculations, establishin...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22263

    authors: Shafiq N,Saleem M,Riaz N,Tousif MI,Jabbar A,Tareen RB,Pescitelli G

    更新日期:2014-01-01 00:00:00

  • (R,R)-N,N'-dimethylcyclohexyl-1,2-diazaseleno-phospholidine as a chiral derivatizing agent for the evaluation of chiral alcohols.

    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

    authors: House KL,O'Connor MJ,Silks LA 3rd,Dunlap RB,Odom JD

    更新日期:1994-01-01 00:00:00

  • Chiral bioanalytical methods in bioequivalence studies of intravenous vs. oral formulations of ibuprofen.

    abstract::According to the Ibuprofen Product-Specific Bioequivalence Guidance of the European Medicines Agency, achiral bioanalytical methods are considered acceptable for demonstration of bioequivalence of ibuprofen-containing products. The aim of this investigation is to compare the bioequivalence outcomes obtained with indiv...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23258

    authors: González-Rojano E,Marcotegui J,Laredo L,Gwaza L,Gordon J,Portolés A,Vargas E,Morales-Alcelay S,García-Arieta A

    更新日期:2020-09-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20482

    authors: Pieraccini S,Ferrarini A,Spada GP

    更新日期:2008-05-15 00:00:00

  • Separation and toxicity of salithion enantiomers.

    abstract::Enantioseletive toxicities of chiral pesticides have become an environmental concern recently. In this study, we evaluated the enantiomeric separation of salithion on a suite of commercial chiral columns and assessed the toxicity of enantiomers toward butyrylcholinesterase and Daphnia magna. Satisfactory separations o...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20690

    authors: Zhou S,Lin K,Li L,Jin M,Ye J,Liu W

    更新日期:2009-11-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23120

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

    更新日期:2019-10-01 00:00:00

  • The possible role of enantiodiscrimination in bilirubin toxicity.

    abstract::The possibility that enantiodiscrimination of bilirubin might be involved in neuronal membrane destabilization, and therefore in bilirubin toxicity, was investigated, by circular dichroism, on model membranes composed of phospholipids. The equilibrium between bilirubin enantiomers is displaced at some extent by the in...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20610

    authors: Bernardini C,D'Arrigo P,Elemento G,Mancini G,Servi S,Sorrenti A

    更新日期:2009-01-01 00:00:00

  • Pharmacokinetics of nateglinide enantiomers and their metabolites in Goto-Kakizaki rats, a model for type 2 diabetes mellitus.

    abstract::The pharmacokinetics of (-)-N-(trans-4-isopropylcyclohexanecarbonyl)-D-phenylalanine (nateglinide) and its enantiomer (L-enantiomer) was studied in Goto-Kakizaki (GK) rats after intravenous administration of nateglinide or L-enantiomer at a dose of 40 micromol/kg body weight. Nateglinide, its L-enantiomer and their me...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20711

    authors: Tamura M,Shiba S,Kudo N,Kawashima Y

    更新日期:2010-01-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10006

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

    更新日期:2001-01-01 00:00:00

  • Successful use of a novel lux® i-Amylose-1 chiral column for enantioseparation of "legal highs" by HPLC.

    abstract::Bath salts, fumigations, cleaners and air fresheners, behind these terms substances are hidden, which count as "Legal Highs". These fancy names are used to pretend Legal Highs as harmless compounds, to circumvent legal regulations for marketing as well as to increase the sales. Besides classic illicit drugs of synthet...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23135

    authors: Kadkhodaei K,Kadisch M,Schmid MG

    更新日期:2020-01-01 00:00:00

  • Use of the exciton chirality method in the investigation of ligand-gated synthetic ion channels.

    abstract::The objective of this brief highlight is to point out the central role of the exciton chirality method to gain insights on the structural basis of the recently achieved ligand gating of synthetic ion channels. This unprecedented ligand gating was achieved with an equally unprecedented transmembrane rigid-rod pi-stack ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20221

    authors: Sakai N,Talukdar P,Matile S

    更新日期:2006-02-01 00:00:00

  • Lack of metabolic racemisation of ropivacaine, determined by liquid chromatography using a chiral AGP column.

    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

    authors: Arvidsson T,Bruce HF,Halldin MM

    更新日期:1995-01-01 00:00:00

  • Highly enantioselective HPLC separations using the covalently bonded macrocyclic antibiotic, ristocetin A, chiral stationary phase.

    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>

    authors: Ekborg-Ott KH,Liu Y,Armstrong DW

    更新日期:1998-01-01 00:00:00

  • Stereoselective pharmacokinetics and metabolism of flobufen in guinea pigs.

    abstract::Stereoselective aspects of pharmacokinetics and metabolism of a chiral nonsteroidal antiinflammatory drug, flobufen, 4-(2', 4'-difluorobiphenyl-4-yl)-2-methyl-4-oxobutanoic acid, were studied in male guinea pigs after p.o. administration of racemic flobufen (rac-flobufen) at a dose of 10 mg/kg. Blood samples were coll...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10288

    authors: Trejtnar F,Král R,Pávek P,Wsól V

    更新日期:2003-10-01 00:00:00

  • Channel-like crystal structure of cinchoninium L-O-phosphoserine salt dihydrate.

    abstract::Studies on the interactions between L-O- phosphoserine, as one of the simplest fragments of membrane components, and the Cinchona alkaloid cinchonine, in the crystalline state were performed. Cinchoninium L-O-phosposerine salt dihydrate (PhSerCin) crystallizes in a monoclinic crystal system, space group P2(1), with un...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20784

    authors: Wesełucha-Birczyńska A,Oleksyn BJ,Watroba J

    更新日期:2010-06-01 00:00:00

  • The first preparation of enantiopure 1-methyl-7-oxabicyclo[2.2.1]heptan-2-one, a versatile chiral building block for terpenoids.

    abstract::Methods for the resolution of (+/-)-1-methyl-7-oxabicyclo[2.2.1]heptan-2-one 1, a versatile chiral building block for terpenoids, have been investigated. While no efficient result was obtained with kinetic resolution methods, both enantiomers of 1 were prepared optically pure for the first time via esterification of t...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20095

    authors: Guan YK,Li YL

    更新日期:2005-02-01 00:00:00

  • Trigonostemons G and H, dinorditerpenoid dimers with axially chiral biaryl linkage from Trigonostemon chinensis.

    abstract::Trigonostemons G and H, two novel dimeric dinorditerpenoids, were isolated from the stem barks of Trigonostemon chinensis. Their planar structures and relative configurations were established by extensive analysis of spectroscopic data. Trigonostemons G and H possess a homodimeric biaryl skeleton obtained from two rea...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23170

    authors: Zhu Q,Tang C,Mándi A,Kurtán T,Ye Y

    更新日期:2020-03-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20873

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

    更新日期:2011-01-01 00:00:00

  • Simultaneous chiral analysis of amphetamine-type stimulants and ephedrine by capillary electrophoresis coupled to time-of-flight mass spectrometry.

    abstract::This study focused on the chiral characteristics of methamphetamine seizures in Shanghai for inferring the synthetic pathways of drugs. Capillary electrophoresis coupled to time-of-flight mass spectrometry was used for simultaneous chiral separation of amphetamine-type stimulants and ephedrine, including S(+)-amphetam...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22987

    authors: Cui X,Liang C,Gong F,Wang R,Ni C,Wu Y,Chen G,Zhang Y

    更新日期:2018-09-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20254

    authors: Dartigalongue T,Hache F

    更新日期:2006-05-05 00:00:00

  • Derivatization, complexation, and absolute configurational assignment of chiral primary amines: application of exciton-coupled circular dichroism.

    abstract::We report here a sensitive method for the determination of the absolute configurations of primary amines using exciton-coupled circular dichroism (ECCD). The method works on a microgram scale by derivatization of chiral amines with quinoline chromophores. Complexation of the chiral ligands with metal ion fixes the geo...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10158

    authors: Zhang J,Holmes AE,Sharma A,Brooks NR,Rarig RS,Zubieta J,Canary JW

    更新日期:2003-02-01 00:00:00

  • Tautomerism of 4-hydroxy-2,5-dimethyl-3(2H)-furanone: evidence for its enantioselective biosynthesis.

    abstract::Chiral natural flavor compounds exhibit characteristic enantiomeric excesses due to stereoselective, enzymatically catalyzed reactions during biogenesis. Although the enzymatic formation of the strawberry key flavor compound 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF; Furaneol(R)) is anticipated, the naturally occurr...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10247

    authors: Raab T,Hauck T,Knecht A,Schmitt U,Holzgrabe U,Schwab W

    更新日期:2003-08-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(2000)12:5/6<346::AID-CHIR8

    authors: Watanabe T,Gridnev ID,Imamoto T

    更新日期:2000-06-01 00:00:00