Chiral separations on polysaccharide stationary phases using polar organic mobile phases.

Abstract:

:About 30% of a chemically diverse set of compounds were found to separate on four polysaccharide chiral stationary phases using polar organic mobile phases. No structural features appeared to correlate to successful separations. Titrations between normal and polar organic mobile phases suggested that separation mechanisms do not differ between these mobile phases. Attempts made to control retention met with varying degrees of success. Addition of hexane to alcohols had minor effects on retention although this was occasionally beneficial. Addition of water to alcohols increased retention. Addition of water to acetonitrile decreased retention. Addition of alcohol to acetonitrile also proved beneficial to the separation of some compounds. Loading studies performed to mimic preparative separations indicated that the benefits of polar organic mobile phases are largely due to increased solubility.

journal_name

Chirality

journal_title

Chirality

authors

Lynam KG,Stringham RW

doi

10.1002/chir.20212

subject

Has Abstract

pub_date

2006-01-01 00:00:00

pages

1-9

issue

1

eissn

0899-0042

issn

1520-636X

journal_volume

18

pub_type

杂志文章
  • 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

  • Base-catalyzed epimerization of the butenolide in annonaceous acetogenins.

    abstract::The elusive epimerization process in the chiral butenolide moiety of Annonaceous acetogenins was examined under several sets of conditions commonly used for elimination leading to the alpha, beta-unsaturated lactone and the results provide practical guidance in choosing elimination conditions. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(2000)12:3<127::AID-CHIR4>3

    authors: Yu Q,Wu Y,Wu YL,Xia LJ,Tang MH

    更新日期:2000-03-01 00:00:00

  • Structure-retention relationship for enantioseparation of selected fluoroquinolones.

    abstract::Fluoroquinolones are popular class of antibiotics with distinct chemical functionality. Most of them are ampholytes with one chiral center. Stereogeneic center is located either in the side ring of Gatifloxacin (GFLX) or in the quinolone core of Ofloxacin (OFLX). These two amphoteric fluoroquinolones have terminal ami...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22861

    authors: Hassan RM,Yehia AM,Saleh OA,El-Azzouny AA,Aboul-Enein HY

    更新日期:2018-06-01 00:00:00

  • Pimarane diterpenes: Natural source, stereochemical configuration, and biological activity.

    abstract::Plants and fungi are seemingly inexhaustible sources of interesting natural products with remarkable structural and biological diversity. One of the most important groups is the terpenes, ubiquitous natural products that are generated by 2 now well-established biosynthetic pathways: the older mevalonate and the more r...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.23009

    authors: Reveglia P,Cimmino A,Masi M,Nocera P,Berova N,Ellestad G,Evidente A

    更新日期:2018-10-01 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

  • 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

  • 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22554

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

    更新日期:2016-03-01 00:00:00

  • Enantioselective catalytic reduction of ketoimines with trichlorosilane promoted by readily available chiral Lewis bases.

    abstract::The straightforward synthesis of a series of enantiomerically pure Lewis basic amides by simple condensation of commercially available enantiopure diamines with picolinic acid is reported. These compounds were shown to promote the enantioselective reduction of ketoimines with trichlorosilane. Working with the model su...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20615

    authors: Guizzetti S,Benaglia M,Cozzi F,Rossi S,Celentano G

    更新日期:2009-01-01 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

  • Stereoselective sulfation of terbutaline by the rat liver cytosol: evaluation of experimental approaches.

    abstract::Little is known about the stereochemistry of sulfation of chiral phenolic drugs. In this study we examined several in vitro approaches to this question, using (+)-, (-)-, or (+/-)-terbutaline as the substrate and the rat liver cytosol as the phenolsulfotransferase enzyme source. The cosubstrate PAPS was either generat...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530010205

    authors: Walle UK,Walle T

    更新日期:1989-01-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22690

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

    更新日期:2017-03-01 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

  • Spectroscopic properties of the nonplanar amide group: a computational study.

    abstract::Experimental studies suggest that amide bond may significantly deviate from planar arrangement even in linear peptides and proteins. In order to find out the extent to which such deviation may influence principal amide spectroscopic properties, we conducted a computational study of nonplanar N-methylacetamide (NMA) co...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20462

    authors: Bednárová L,Malon P,Bour P

    更新日期:2007-11-01 00:00:00

  • Plasmonic nanoparticles assemblies templated by helical bacteria and resulting optical activity.

    abstract::Plasmonic nanoparticles (NPs) adsorbing onto helical bacteria can lead to formation of NP helicoids with micron scale pitch. Associated chiroptical effects can be utilized as bioanalytical tool for bacterial detection and better understanding of the spectral behavior of helical self-assembled structures with different...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23225

    authors: Feng W,Kadiyala U,Yan J,Wang Y,DiRita VJ,VanEpps JS,Kotov NA

    更新日期:2020-07-01 00:00:00

  • Demonstration of spontaneous chiral symmetry breaking in asymmetric Mannich and Aldol reactions.

    abstract::Spontaneous symmetry breaking in reactive systems, known as a rare physical phenomenon and for the Soai autocatalytic irreversible reaction, might in principle also occur in other, more common asymmetric reactions when the chiral product is capable to promote its formation and an element of "nonlinearity" is involved ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20474

    authors: Mauksch M,Tsogoeva SB,Wei S,Martynova IM

    更新日期:2007-11-01 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 ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530060508

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

    更新日期:1994-01-01 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

  • Noncovalent immobilization of ionic-tagged box-Cu(OAc)2 complex and its application in asymmetric Henry reaction.

    abstract::Immobilized Cu(OAc)(2)-bis(oxazolines) via hydrogen bonding by SBA-15 was applied to asymmetric Henry reaction, and good enantioselectivities were obtained (up to 83% ee) between 2-methoxybenzaldehyde and CH(3)NO(2) in isopropyl alcohol (iPrOH). The catalyst could be reused seven times without any obvious loss in enan...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22104

    authors: Li ZH,Zhou ZM,Hao XY,Zhang J,Dong X,Liu YQ

    更新日期:2012-12-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1999)11:9<694::AID-CHIR5>3

    authors: Redondo J,Blázquez MA,Torrens A

    更新日期:1999-01-01 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

  • Alpha-aminophosphonates as novel organocatalysts for asymmetric Michael addition of carbonyl compounds to nitroolefins.

    abstract::A cyclic alpha-aminophosphonate was found to be a novel organocatalyst for Michael type addition reactions of carbonyl compounds to nitroolefins to afford the corresponding adducts in high enantio- and diastereoselectivities. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20552

    authors: Tao Q,Tang G,Lin K,Zhao YF

    更新日期:2008-07-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22434

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

    更新日期:2015-05-01 00:00:00

  • Chiral recognition ability and solvent versatility of bonded amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase: enantioselective liquid chromatographic resolution of racemic N-alkylated barbiturates and thalidomide analogs.

    abstract::The chiral recognition ability and solvent versatility of a new chiral stationary phase containing amylose 3,5-dimethylphenylcarabamate immobilized onto silica gel (CHIRALPAK IA) is investigated. Thus, the direct enantioselective separation of a set of racemic N-alkylated barbiturates and 3-alkylated analogs of thalid...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20398

    authors: Ghanem A,Al-Humaidi E

    更新日期:2007-06-01 00:00:00

  • Unusual temperature-induced retention behavior of constrained β-amino acid enantiomers on the zwitterionic chiral stationary phases ZWIX(+) and ZWIX(-).

    abstract::The effects of temperature on the chiral recognition of cyclic β-amino acid enantiomers on zwitterionic [Chiralpak ZWIX(+) and ZWIX(-)] chiral stationary phases were investigated. Experiments were performed at different mobile phase compositions and under 10°C column temperature increments in the temperature range 10-...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22333

    authors: Ilisz I,Pataj Z,Gecse Z,Szakonyi Z,Fülöp F,Lindner W,Péter A

    更新日期:2014-08-01 00:00:00

  • Discrimination of chiral guests by chiral channels: variable temperature studies by SXRD and solid state 13C NMR of the deoxycholic acid complexes of camphorquinone and endo-3-bromocamphor.

    abstract::3alpha,12alpha-dihydroxy-5beta-cholan-24-oic acid (deoxycholic acid DCA) is able to discriminate between the R- and S-enantiomers of camphorquinone and endo-(+)-3-bromocamphor and select only the S-enantiomers from a racemic mixture. DCA forms novel well ordered 1:1 adducts with (1S)-(+)-camphorquinone and (1S)-endo-(...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20561

    authors: Tahir MI,Rees NH,Heyes SJ,Cowley AR,Prout K

    更新日期:2008-07-01 00:00:00

  • Role of latent heat in chiral symmetry breaking transition in the crystallization of 1,1'-binaphthyl.

    abstract::The influence of latent heat dissipated by the crystallization of 1,1'-binaphthyl in its supercooled molten state on the chiral symmetry breaking transition was investigated. Temperature change in the crystallization system was monitored by infrared thermocamera. Temperature rise due to the dissipation of latent heat ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10187

    authors: Asakura K,Hayashi M,Osanai S

    更新日期:2003-03-01 00:00:00

  • Catalytic asymmetric synthesis of 19,20-dihydroakuammicine.

    abstract::An enantiocontrolled total synthesis of 19,20-dihydroakuammicine using a catalytic asymmetric Michael addition of dimethyl malonate to cyclohexenone as the key step is described. The above catalytic asymmetric Michael addition proceeds quite efficiently in the presence of a heterobimetalic asymmetric catalyst (ALB-KO-...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(2000)12:5/6<400::AID-CHIR1

    authors: Ohori K,Shimizu S,Ohshima T,Shibasaki M

    更新日期:2000-06-01 00:00:00

  • Nonlinear chiral interactions in resolutions with benzylamine derivatives.

    abstract::N-formylphenylalanine was subjected to optical resolution using a chiral agent such as phenylethylamine enantiomer, (R)-phenylglycine methyl ester, (S)-N-benzyl-2-aminobutanol, alone or in a mixture with each other or in a mixture with benzylamine. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20330

    authors: Pálovics E,Fogassy E,Schindler J,Nógrádi M

    更新日期:2007-01-01 00:00:00

  • Deracemization of an axially chiral biphenylic derivative as a tool for investigating chiral recognition in self-assemblies.

    abstract::Two diastereomeric cationic surfactants derived from L-proline, in which the second chiral center is a quaternary nitrogen, have been separated and fully characterized. The recognition properties of the aggregates formed by the two diastereomeric surfactants have been investigated by circular dichroism and (1)H NMR th...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10230

    authors: Borocci S,Ceccacci F,Galantini L,Mancini G,Monti D,Scipioni A,Venanzi M

    更新日期:2003-05-15 00:00:00

  • Short step enantioselective synthesis of (-)-swainsonine.

    abstract::Recent discovery of asymmetric desymmetrization of meso-heterocycles using (R,R)-(salen)manganese complex 2 as a catalyst allowed easy access to optically active 2,3,4-trisubstituted pyrrolidines. Taking advantage of this new reaction, we could achieve the short-step synthesis of (-)-swainsonine 1. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(2000)12:5/6<464::AID-CHIR2

    authors: Punniyamurthy T,Irie R,Katsuki T

    更新日期:2000-06-01 00:00:00