CHIRBASE, a graphical molecular database on the separation of enantiomers by liquid-, supercritical fluid-, and gas chromatography.

Abstract:

:In order to cope with the increasing number of publications on the separation of enantiomers by chromatography on a chiral stationary phase, the graphical molecular database CHIRBASE was created. In the present state, the database package covers information (structural, bibliographic, and chromatographic data) on liquid-, supercritical fluid-, and gas chromatography; other methods will follow. CHIRBASE, running on the MDL software Chembase, meets the requirements of contemporary information management in the chemical and pharmaceutical industry. (Detailed information including a demo-version of each part of CHIRBASE can be obtained from the authors on request).

journal_name

Chirality

journal_title

Chirality

authors

Koppenhoefer B,Nothdurft A,Pierrot-Sanders J,Piras P,Popescu C,Roussel C,Stiebler M,Trettin U

doi

10.1002/chir.530050404

subject

Has Abstract

pub_date

1993-01-01 00:00:00

pages

213-9

issue

4

eissn

0899-0042

issn

1520-636X

journal_volume

5

pub_type

杂志文章
  • 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

  • Stereoselective renal secretion of carbenicillin in rabbits: role of the organic anion transporter at the renal brush border membrane.

    abstract::Stereoselectivity in the renal secretion of carbenicillin (CBPC) was studied in rabbits. Significant renal secretion of CBPC was observed in vivo, with the secretion of the S-epimer being greater than that of the R-epimer. Stereoselective transport of CBPC was further studied in vitro using basolateral and brush borde...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1998)10:4<349::AID-CHIR10>

    authors: Itoh T,Nakaura H,Koyano S,Tsuda Y,Yamada H

    更新日期:1998-01-01 00:00:00

  • Helicity of perfluoroalkyl chains controlled by the self-assembly of the Ala-Ala dipeptides.

    abstract::Four Ala-Ala dipeptides with a perfluoroalkyl chain at the N-terminal were synthesized. They were able to self-assemble into helical nanofibers and/or twisted nanobelts in a mixture of DMSO/H2 O. The handedness of nanofibers and nanobelts was controlled by the chirality of the alanine at the N-terminal. The stacking h...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23130

    authors: Zhang L,Lin S,Tong Q,Li Y,Wang Y,Li Y,Li B,Yang Y

    更新日期:2019-11-01 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

  • 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. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10091

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

    更新日期:2002-07-01 00:00:00

  • Viewing and inducing symmetry breaking at the single-molecule limit.

    abstract::Symmetry breaking by photons, electrons, and molecular interactions lies at the heart of many important problems as varied as the origin of homochiral life to enantioselective drug production. Herein we report a system in which symmetry breaking can be induced and measured in situ at the single-molecule level using sc...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22096

    authors: Tierney HL,Jewell AD,Baber AE,Iski EV,Sykes EC

    更新日期:2012-12-01 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....

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23201

    authors: Jintoku H,Ihara H

    更新日期:2020-05-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20274

    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

  • 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

  • Structure and unexpected chiroptical properties of chiral 4-pyrrolidinyl substituted 2(5H)-furanones.

    abstract::Planar 2(5H)-furanones substituted at C4 with a chiral pyrrolidinyl group show CD spectra which are apparently due to the distortion of the C4-N1 bond of sp2 character from the plane defined by the 2(5H)-furanone ring atoms and/or due to the presence of substituents in the pyrrolidine ring. This is a new, previously n...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20059

    authors: Gawroński J,Gawrońska K,Kwit M,Kacprzak K,Rychlewska U

    更新日期:2004-08-01 00:00:00

  • Simulated moving columns technique for enantioselective supercritical fluid chromatography.

    abstract::This article describes a very useful extension of an unique column switching technique called "Simulated Moving Columns" (SMC) that was previously reported for chiral high performance liquid chromatography (HPLC) (Zhang and McConnell, Journal of Chromatography A 2004;1028:227-238). SMC uses two or three short chiral c...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20409

    authors: Zhang Y,Dai J,Wang-Iverson DB,Tymiak AA

    更新日期:2007-09-01 00:00:00

  • Stereoselective chiral inversion of pantoprazole enantiomers after separate doses to rats.

    abstract::(+/-)-Pantoprazole ((+/-)-PAN), (+/-)-5-(difluoromethoxy)-2-[[3.4-dimethoxy-2-pyridinyl)methyl]sul finyl]- 1H-benzimidazole) is a chiral sulfoxide that is used clinically as a racemic mixture. The disposition kinetics of (+)-PAN and (-)-PAN given separately has been studied in rats. Serum levels of (+)- and (-)-PAN an...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1998)10:8<747::AID-CHIR5>3

    authors: Masubuchi N,Yamazaki H,Tanaka M

    更新日期:1998-01-01 00:00:00

  • Stereoselective intramolecular cyclization to 4-(hydroxymethyl)-3-(1H-indolyl)oxazolidin-2-ones.

    abstract::A simple high-yield three-steps route to optically active 4-hydroxymethyl-3-(1H-indolyl)oxazolidin-2-ones from (S)-glycidol is described. The key intermediates (R)-oxiran-2-ylmethyl 1H-indol-4/-5-ylcarbamates are obtained in high yields from (S)-glycidol. These are readily transformed to oxazolidin-2-ones, very intere...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22003

    authors: Chiummiento L,Funicello M,Tramutola F

    更新日期:2012-04-01 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 ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20518

    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

  • Strategic use of preparative chiral chromatography for the synthesis of a preclinical pharmaceutical candidate.

    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

    authors: Leonard WR Jr,Henderson DW,Miller RA,Spencer GA,Sudah OS,Biba M,Welch CJ

    更新日期:2007-09-01 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

  • 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 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22456

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

    更新日期:2015-07-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23167

    authors: Liu W,Holdsworth C,Ye L

    更新日期:2020-03-01 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

  • Additional criterion for the determination of the handedness of 2(1) helices in crystals of bile acids: Crystal structure of a tert-butylphenyl derivative of cholic acid.

    abstract::[3β,5β,7α,12α]-3-(4-t-Butylbenzoilamine)-7,12-dihydroxycholan-24-oic acid was synthesized and recrystallized from chlorobenzene and acetone. Orthorhombic P2(1)2(1)2(1) and monoclinic P2(1) crystals were obtained, respectively, and both crystals include solvent and water molecules with a 1:1:1 stoichiometry. In the sec...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.21020

    authors: Meijide F,Trillo JV,Soto VH,Jover A,Tato JV

    更新日期:2011-11-01 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 ...

    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

  • 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

  • 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 ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.1063

    authors: King RB

    更新日期:2001-08-01 00:00:00

  • Chiral aggregates and asymmetric induction of the reduction of prochiral ketones.

    abstract::The aim of this work was to establish structure-reactivity relationships between chiral aggregates (micelles, vesicles, and "pseudo-micelles" of amphiphilic dendrimers) and asymmetric induction. In water, micelles or vesicles formed with sugar-headed surfactants gave less than 10% ee in the reduction of prochiral keto...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/1520-636X(2001)13:1<24::AID-CHIR5>3.0.CO;2

    authors: Rico-Lattes I I,Schmitzer A,Perez E,Lattes A

    更新日期:2001-01-01 00:00:00

  • Organocatalytic aza-Michael/retro-aza-Michael reaction: pronounced chirality amplification in aza-Michael reaction and racemization via retro-aza-Michael reaction.

    abstract::A detailed experimental investigation of an aza-Michael reaction of aniline and chalcone is presented. A series of Cinchona alkaloid-derived organocatalysts with different functional groups were prepared and used in the aza-Michael and retro-aza-Michael reaction. There was an interesting finding that a complete revers...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20940

    authors: Cai YF,Li L,Luo MX,Yang KF,Lai GQ,Jiang JX,Xu LW

    更新日期:2011-05-01 00:00:00

  • Enantioselective synthesis of 2- and 3-substituted 2,3-dihydro[1,4]dioxino[2,3-b]pyridine derivatives and enantiomeric purity control by capillary electrophoresis.

    abstract::A rapid and simple procedure for enantioselective preparation of 2- and 3-substituted 2,3-dihydro[1,4]dioxino[2,3-b]pyridine derivatives (A and B, respectively) is described. The enantiomeric purity of each isomer was determined by capillary electrophoresis using a dual-cyclodextrin system (S-beta-CD/beta-CD) dissolve...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20090

    authors: Lazar S,Soukri M,El Haddad M,Akssira M,Leger JM,Jarry C,Morin P,Guillaumet G

    更新日期:2005-01-01 00:00:00

  • Chiral separation and CD characterisation of enantiomeric cyclotriphosphazene derivatives.

    abstract::The gem-disubstituted cyclotriphosphazene 1 reacted with piperazine (pip) to give the piperazine-bridged derivative 2, which is expected to exist in meso and racemic forms because the two PCl (pip) groups are stereogenic. The proton-decoupled (31)P NMR spectrum of 2 gave rise to two similar sets of ABX signals in a 1:...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20187

    authors: Bui TT,Coles SJ,Davies DB,Drake AF,Eaton RJ,Hursthouse MB,Kiliç A,Shaw RA,Yeşilot S

    更新日期:2005-10-01 00:00:00

  • Optically active α-phenylethylamine as efficient organocatalyst in the solvent-free reactions between 2,3-butanedione and conjugated nitroolefins.

    abstract::(R)-(+) and (S)-(-)-1-phenylethylamine have been shown to promote highly diastereoselective and complementary enantioselective formal [3 + 2]carbocyclization reactions between 2,3-butanedione and conjugated nitroalkenes with formation of enantiomerically rich 2-hydroxy-3-nitrocyclopentanone derivatives. The reactions ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22088

    authors: Felluga F,Forzato C,Nitti P,Pitacco G,Prati F,Valentin E,Zangrando E

    更新日期:2012-12-01 00:00:00

  • Chirality as an inherent general property of matter.

    abstract::A statement has been formulated that chirality is an indispensable inherent property of all material objects, at one level of organization of matter or another. The translation of chirality from one level of material objects to another deserves our attention. The parity violation of weak interactions can be discussed ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20271

    authors: Davankov V

    更新日期:2006-08-01 00:00:00