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 selectivity of this CSP were examined in each mode. Optimization of separations on this column is discussed. The ristocetin A CSP appeared to be complimentary to other glycopeptide CSPs (i.e., vancomycin and teicoplanin). Column stability was excellent. The CSP was not irreversibly altered when going from one mobile phase to another.

journal_name

Chirality

journal_title

Chirality

authors

Ekborg-Ott KH,Liu Y,Armstrong DW

doi

10.1002/(SICI)1520-636X(1998)10:5<434::AID-CHIR10>

subject

Has Abstract

pub_date

1998-01-01 00:00:00

pages

434-83

issue

5

eissn

0899-0042

issn

1520-636X

pii

10.1002/(SICI)1520-636X(1998)10:5<434::AID-CHIR10>

journal_volume

10

pub_type

杂志文章
  • Highly enantiomeric reduction of acetophenone and its derivatives by locally isolated Rhodotorula glutinis.

    abstract::Ninety isolates of microorganisms belonging to different taxonomical groups (30 bacteria, 20 yeast, and 40 fungi) were previously isolated from various samples. These isolates were screened as reducing agents for acetophenone 1a to phenylethanol 2a. It was found that the isolate EBK-10 was the most effective biocataly...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20846

    authors: Zilbeyaz K,Kurbanoglu EB

    更新日期:2010-10-01 00:00:00

  • An integrating sphere to measure CD from difficult samples

    abstract::Integrating spheres are widely used with UV-Vis and occasionally with infrared spectrophotometers to measure different types of samples, either in transmission mode (scattered transmission accessories) or in total/diffuse reflectance mode. We built a prototype sphere of the demountable type, which fits easily the samp...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(2000)12:4<291::AID-CHIR16>

    authors: Castiglioni E,Albertini P

    更新日期:2000-05-01 00:00:00

  • Enhanced efficiency due to the use of achiral additives in the optical resolution of 1-phenylethylamine by its glutaric acid derivative.

    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

    authors: Schindler J,Egressy M,Bereczki L,Pokol G,Fogassy E,Marthi K

    更新日期:2007-03-01 00:00:00

  • Structural Features and Asymmetric Environment of i-Pr-SPRIX Ligand.

    abstract::Novel chiral diisopropyl spiro bis(isoxazoline) ligands, anti-i-Pr-SPRIX and syn-i-Pr-SPRIX, were designed and synthesized. Their catalytic utility, X-ray crystallographic analyses, and complexation studies demonstrated the structural features of tetraisopropyl spiro bis(isoxazoline) ligand, i-Pr-SPRIX, which is a pro...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22467

    authors: Takenaka K,Lin X,Takizawa S,Sasai H

    更新日期:2015-08-01 00:00:00

  • Chiroptical properties of diamino carboxylic acids.

    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

    authors: Bredehöft JH,Breme K,Meierhenrich UJ,Hoffmann SV,Thiemann WH

    更新日期:2007-07-01 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

  • Chemoenzymatic approach to optically active 4-hydroxy-5-alkylcyclopent-2-en-1-one derivatives: an application of a combined circular dichroism spectroscopy and DFT calculations to assignment of absolute configuration.

    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

    authors: Frelek J,Karchier M,Madej D,Michalak K,Różański P,Wicha J

    更新日期:2014-06-01 00:00:00

  • Online sample concentration in partial-filling chiral electrokinetic chromatography – mass spectrometry.

    abstract::The concentration sensitivity of a racemic drug (chlorpheniramine maleate) in chiral capillary electrophoresis with electrospray ionization – mass spectrometric detection was improved ~500-fold via stacking. Enantiomeric separation was achieved through the use of a neutral chiral pseudostationary phase (2-hydroxpropyl...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22257

    authors: Wuethrich A,Haddad PR,Quirino JP

    更新日期:2014-11-01 00:00:00

  • Enantioseparation of napropamide by supercritical fluid chromatography: Effects of the chromatographic conditions and separation mechanism.

    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 . I...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22836

    authors: Zhao L,Xie J,Guo F,Liu K

    更新日期:2018-05-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530040607

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

    更新日期:1992-01-01 00:00:00

  • Role of the weak interactions in enantiorecognition of racemic dihydropyrimidinones by novel brush-type chiral stationary phases.

    abstract::The chiral discrimination ability of two recently prepared chiral stationary phases (CSP 1 and CSP 2), based on a leucine derived chiral selector, was tested for the enantiomers of dihydropyrimidone (DHPM) derivatives and compared with the commercially available Hyun-leucine CSP 3 and classical Pirkle-leucine CSP 4. B...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20396

    authors: Forjan DM,Gazić I,Vinković V

    更新日期:2007-06-01 00:00:00

  • Single-walled carbon nanotube absolute-handedness chirality assignment confirmation using metalized porphyrin's supramolecular structures via STM imaging technique.

    abstract::This work reports confirmation of the experimental assignment of the absolute-handedness chirality of single-walled carbon nanotubes (SWNTs). This was achieved by applying the scanning tunneling microscopy (STM) imaging technique to a supramolecular composite consisting of a metalized porphyrin derivative (nickel-5,15...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23163

    authors: Abd El-Mageed AIA,Ogawa T

    更新日期:2020-03-01 00:00:00

  • Chiral counter-current chromatography: A survey of its instrument, mechanism, procedure, and applications.

    abstract::The chiral separation by counter-current chromatography has made great progress in the past three decades. It has become increasingly popular in the field of chiral separation, and many applications have been introduced during the last years. This review mainly focuses on the current topics, applications, and trends i...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.23262

    authors: Duan WD,Huang XY,Di DL

    更新日期:2020-10-01 00:00:00

  • High-performance liquid chromatographic enantioseparation of Betti base analogs on a newly developed isopropyl carbamate-cyclofructan6-based chiral stationary phase.

    abstract::The direct separation of the enantiomers of 1-(α-aminoarylmethyl)-2-naphthol, 1-(α-aminoalkyl)-2-naphthol, 2-(α-aminoarylmethyl)-1-naphthol analogs, and 2-(1-amino-2-methylpropyl)-1-naphthol) was performed on a newly developed chiral stationary phase containing isopropyl carbamate-cyclofructan6 as chiral selector, wit...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20968

    authors: Aranyi A,Ilisz I,Pataj Z,Szatmári I,Fülöp F,Armstrong DW,Péter A

    更新日期:2011-08-01 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

  • 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22039

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

    更新日期:2012-05-01 00:00:00

  • Enantioselective determination of isradipine in human serum using chiral stationary phase liquid chromatography and gas chromatography with nitrogen selective detection.

    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

    authors: Rask HS,Angelo HR,Christensen HR

    更新日期:1998-01-01 00:00:00

  • Conformational spaces of Cinchona alkaloids.

    abstract::A systematic and comprehensive study of the conformational spaces of the Cinchona alkaloids quinine, quinidine, cinchonine, cinchonidine, epiquinine, epiquinidine, epicinchonine, and epicinchonidine using the semiempirical PM3 method is described. The results were analyzed in terms of syn/anti and open/closed/hindered...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10265

    authors: Caner H,Biedermann PU,Agranat I

    更新日期:2003-08-01 00:00:00

  • Stereospecific pH-dependent degradation kinetics of R- and S-naproxen-beta-l-O-acyl-glucuronide.

    abstract::The hydrolysis and acyl migration of biosynthetic S-naproxen-beta-l-O-acyl glucuronide (I) and R-naproxen-beta-l-O-acyl glucuronide (II) was followed by HPLC. Nine first-order kinetic rate constants for the hydrolysis and acyl migration between the beta-l-O-acyl glucuronide, its alpha/beta-2, alpha/beta-3-, alpha/beta...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10047

    authors: Mortensen RW,Sidelmann UG,Tjørnelund J,Hansen SH

    更新日期:2002-05-05 00:00:00

  • Isothermal titration calorimetry for chiral chemistry.

    abstract::One of the most powerful techniques that are currently available to measure thermodynamic parameters such as enthalpy (ΔH), Gibbs free energy (ΔG), entropy changes (ΔS), and binding affinity in chemical reactions is isothermal titration calorimetry (ITC). Recent advances in instrumentation have facilitated the develop...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.22842

    authors: Werber L,Mastai Y

    更新日期:2018-05-01 00:00:00

  • Secondary phosphine oxides: tautomerism and chiral recognition monitored by multinuclear NMR spectroscopy of their Rh2[(R)-MTPA]4 adducts.

    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

    authors: Magiera D,Szmigielska A,Pietrusiewicz KM,Duddeck H

    更新日期:2004-01-01 00:00:00

  • Excavations in drug chirality: 1. Cyclothiazide.

    abstract::There is a great deal of current interest in the role and importance of chirality in the development of new drugs, but little attention is being paid to the stereochemistry of older drugs. Indeed, many older chiral drugs were introduced without adequate information on their stereochemical identity or composition. We h...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530030103

    authors: Nusser E,Banerjee A,Gal J

    更新日期:1991-01-01 00:00:00

  • Synthesis of Novel Chiral Sulfonamide-Bearing 1,2,4-Triazole-3-thione Analogs Derived from D- and L-Phenylalanine Esters as Potential Anti-Influenza Agents.

    abstract::Novel enantiopure 1,2,4-trizole-3-thiones containing a benzensulfonamide moiety were synthesized via multistep reaction sequence starting with D-phenylalanine methyl ester and L-phenylalanine ethyl ester as a source of chirality. The chemical structures of all compounds were characterized by elemental analysis, UV, IR...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22607

    authors: Başaran E,Karaküçük-Iyidoğan A,Schols D,Oruç-Emre EE

    更新日期:2016-06-01 00:00:00

  • Optical resolution of 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline by supercritical fluid extraction.

    abstract::6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (FTHQ) enantiomers were separated by supercritical fluid extraction using carbon dioxide. Diastereoisomeric salts were formed from the racemic base with less than one equivalent of O,O'-di-(4-toluoyl)-(2R,3R)-tartaric acid (DPTTA). Further purification was achieved by part...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.1178

    authors: Kmecz I,Simándi B,Bálint J,Székely E,Fogassy E,Kemény S

    更新日期:2001-01-01 00:00:00

  • Asymmetric allylation of α-ketoester-derived N-benzoylhydrazones promoted by chiral sulfoxides/N-oxides Lewis bases: highly enantioselective synthesis of quaternary α-substituted α-allyl-α-amino acids.

    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

    authors: Reyes-Rangel G,Bandala Y,García-Flores F,Juaristi E

    更新日期:2013-09-01 00:00:00

  • Discrimination of enantiomers of alpha-amino acids by chiral derivatizing reagents from trans-1,2-diaminocyclohexane.

    abstract::New chiral derivatizing reagents (CDAs) derived from trans-1,2-diaminocyclohexane, having an electron-deficient aromatic substituent (either an aromatic imide or 3,5-dinitrobenzamide) and rigid structure (either an amide or a urea linker), are reported. Significant shift differences of diastereotopic protons in the 1H...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20435

    authors: Kaik M,Gajewy J,Grajewski J,Gawronski J

    更新日期:2008-03-01 00:00:00

  • The biological activities of prothioconazole enantiomers and their toxicity assessment on aquatic organisms.

    abstract::Chiral fungicide prothioconazole has a wide range of antifungal spectrum; however, little research has been conducted to evaluate prothioconazole on an enantiomeric level. Five target pathogens and three common aquatic organisms were tested for the enantioselective bioactivity and toxicity of prothioconazole in this w...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23075

    authors: Zhai W,Zhang L,Cui J,Wei Y,Wang P,Liu D,Zhou Z

    更新日期:2019-06-01 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

  • 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1999)11:2<85::AID-CHIR1>3.

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

    更新日期:1999-01-01 00:00:00

  • Asymmetric Diels-Alder reaction involving chiral benzimidazoles as organocatalysts.

    abstract::(S)-(-)-2-(α-hydroxyethyl)-benzimidazole and (S)-(+)-2-(α-hydroxybenzyl)-benzimidazole work as chiral Brønsted bases (BBs) in Diels-Alder reaction between anthrone and maleimides under mild reaction condition. These chiral BBs cause asymmetric induction. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20942

    authors: Mirgane NA,Karnik AV

    更新日期:2011-05-01 00:00:00