Discrimination in resolving systems: ephedrine-mandelic acid.

Abstract:

:Resolution of mandelic acid with (-)-(1R,2S)-ephedrine in water and ethanol produces intermediate diastereomeric salts with greatly disparate solubilities and melting points. Single crystal X-ray analysis of the less (L) and more (M) soluble (-)-ephedrinium mandelates (I, II) shows crystal structures which are isosteric, each crystallizing in the monoclinic system, space group C2. Protonated ephedrines occupy the same relative positions in the L- and M-salts, and mandelates are in the same general locations. Hydrogen bonds link alternating protonated ephedrine nitrogens and mandelate carboxylate oxygens in each salt forming columns of ions. The helical H-bonded chain winds down the crystallographic 2-fold screw axis. Additional H-bonds form between 2-fold related mandelates in the L-salt. Mixed crystals, containing both mandelate isomers, (2R)- and (2S)-mandelates, are obtained from the resolving system partly depleted of the L-salt. A specimen with nearly equal amounts of the mandelates (III) is also isosteric with the commensurate structures. I (294K), L-salt: a = 18.160(7), b = 6.538(2), c = 13.898(4) A, beta = 92.02(3) degrees, V = 1649.1(9) A3; IIa (294K), M-salt: a = 17.978(11), b = 7.164(4), c = 13.574(6)A, beta = 96.41(4) degrees, V = 1737.3(16) A3; IIb (223K), M-salt: a = 17.805(8), b = 7.115(2), c = 13.50(5) A, beta = 96.89(3) degrees, V = 1697.9(15) A3; III (294K), mixed-salt: a = 18.184(22), b = 6.792(7), c = 13.808(19) A, beta = 93.74(10) degrees, V = 1701.7(35) A3.

journal_name

Chirality

journal_title

Chirality

authors

Valente EJ,Zubkowski J,Eggleston DS

doi

10.1002/chir.530040807

subject

Has Abstract

pub_date

1992-01-01 00:00:00

pages

494-504

issue

8

eissn

0899-0042

issn

1520-636X

journal_volume

4

pub_type

杂志文章
  • Bi-directional chiral inversion of ketoprofen in CD-1 mice.

    abstract::The R enantiomers of some of the 2-arylpropionic acid non-steroidal antiinflammatory drugs (NSAIDs) are known to undergo metabolic chiral inversion to their more pharmacologically active antipodes. This process is drug and species dependent and usually unidirectional. The S to R chiral inversion, on the other hand, is...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1997)9:1<29::AID-CHIR6>3.0

    authors: Jamali F,Lovlin R,Aberg G

    更新日期:1997-01-01 00:00:00

  • Enantiomer self-disproportionation and chiral stationary phase based selective chiral separation of organic compounds.

    abstract::In modern chromatography, chiral stationary phase (CSP) and enantiomer self-disproportionation (ESD) are new inventions of packing material offer a guarantee for a successful enantiomeric separation. All CSPs were synthesized by chemical bonding of the relevant organic moieties onto a porous parent silica material for...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20917

    authors: Mayani VJ,Abdi SH,Mayani SV,Kim HC,Park SK

    更新日期:2011-04-01 00:00:00

  • Circular dichroism of tocopherols versus tocotrienols.

    abstract::Vitamin E is an essential nutrient of still increasing economic importance. Vitamin E derivatives include many nonracemic chiral compounds whose chirooptical characterization is scarcely described in the literature. We report the CD spectra of delta-tocopherol and its unsaturated analog delta-tocotrienol. TDDFT calcul...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20591

    authors: Mazzini F,Pescitelli G,Di Bari L,Netscher T,Salvadori P

    更新日期:2009-01-01 00:00:00

  • Versatile precursor to ruthenium-bis(phosphine) hydrogenation catalysts.

    abstract::The known complex trans-RuCl2(NBD)Py2 (1, NBD is norbornadiene, Py is pyridine) reacts with either (R)-BINAP ((R)-2, 2'-bis(diphenylphosphino)-1,1'-binaphthyl), (S;S)-Chiraphos ((2S;3S-(-)-2,3-bis(diphenylphosphino)butane), (S;S)-Skewphos ((2S;4S)-(-)-2,4-bis(diphenylphosphino)pentane), (R)-(S)-Josiphos ((R)-(-)-1-[(S...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(2000)12:5/6<514::AID-CHIR3

    authors: Akotsi OM,Metera K,Reid RD,McDonald R,Bergens SH

    更新日期:2000-06-01 00:00:00

  • Enantioselective disposition of PCB 136 (2,2',3,3',6,6'-hexachlorobiphenyl) in C57BL/6 mice after oral and intraperitoneal administration.

    abstract::Studies of xenobiotic disposition in rodents often employ experimental designs using differing routes of administration. In an effort to investigate the effects of route of administration on enantioselective disposition of xenobiotics, a chiral polychlorinated biphenyl (PCB), racemic PCB 136, was administered as a sin...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20342

    authors: Kania-Korwel I,Shaikh NS,Hornbuckle KC,Robertson LW,Lehmler HJ

    更新日期:2007-01-01 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...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/(SICI)1520-636X(1996)8:1<35::AID-CHIR8>3.0

    authors: Triggle DJ

    更新日期:1996-01-01 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

  • Metabolic chiral inversion of ibuprofen in isolated rat hepatocytes.

    abstract::Ibuprofen was used to demonstrate that isolated rat hepatocytes offer a suitable in vitro model to investigate the metabolic chiral inversion of anti-inflammatory 2-arylpropionic acids (profens). The inversion of the pharmacologically inactive (-)-(R)-ibuprofen to the active (+)-(S)-ibuprofen was shown to obey apparen...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530020203

    authors: Müller S,Mayer JM,Etter JC,Testa B

    更新日期:1990-01-01 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

  • An efficient dipeptide-catalyzed direct asymmetric aldol reaction of equimolar reactants in solid media.

    abstract::The direct asymmetric aldol reactions of equivalent molar amounts of aldehydes and ketones were carried out at -20 degrees C over alkaline Al(2)O(3) with 20 mol % of Pro-Trp as catalyst and 20 mol % of N-methylmorpholine or 1,4-diazabicyclo[2.2.2]octane as additive. After simple and environmentally friendly work-up, m...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20783

    authors: Lei M,Xia S,Wang J,Ge Z,Cheng T,Li R

    更新日期:2010-06-01 00:00:00

  • Solid-state circular dichroism and hydrogen bonding, part 2: the case of hypothemycin re-investigated.

    abstract::The impact of crystalline forces on the solid-state circular dichroism (CD) spectrum of hypothemycin (), a biologically active molecule extracted from natural sources, has been analyzed by means of time-dependent density functional theory CD calculations. Input structures were extracted from the X-ray geometry of and ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22008

    authors: Pescitelli G

    更新日期:2012-09-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10269

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

    更新日期:2003-01-01 00:00:00

  • Chiral analysis of butaclamol enantiomers in human plasma by HPLC using a macrocyclic antibiotic (vancomycin) chiral stationary phase and solid phase extraction.

    abstract::An enantioseparation of the antipsychotic drug butaclamol in human plasma by high-performance liquid chromatography (HPLC) with solid phase extraction is presented. The separation was achieved on the vancomycin macrocyclic antibiotic chiral stationary phase (CSP) Chirobiotic V with a polar ionic mobile phase (PIM) con...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20001

    authors: Aboul-Enein HY,Hefnawy MM

    更新日期:2004-03-01 00:00:00

  • Separation and aquatic toxicity of enantiomers of synthetic pyrethroid insecticides.

    abstract::Synthetic pyrethroid insecticides are chiral compounds with multiple asymmetric positions. In this study, isomers of four commonly used pyrethroids were separated at the enantiomeric level by enantioselective high-performance liquid chromatography (HPLC), and differences between enantiomers in aquatic toxicity were ch...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20122

    authors: Liu W,Gan JJ,Qin S

    更新日期:2005-01-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20034

    authors: Sakai N,Matile S

    更新日期:2004-01-01 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

  • Stereochemical study of tolperisone, a muscle relaxant agent, by circular dichroism and ultraviolet spectroscopy.

    abstract::The stereochemistry of tolperisone, a chiral aryl-alkyl basic ketone was investigated by means of circular dichroism (CD) and ultraviolet (UV) spectroscopy. The unusually high optical activity of tolperisone hydrochloride in the n-->pi* region is interpreted by the presence of a chiral conformer in solution. For stere...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/1520-636X(2000)12:10<720::AID-CHIR4>3.0.CO

    authors: Zsila F,Hollósi M,Gergely A

    更新日期:2000-11-01 00:00:00

  • Stereochemical analysis of β-keto sulfoxides by circular dichroism.

    abstract::Three β-keto sulfoxides (1-3) were synthesized in enantiopure form and investigated by means of circular dichroism (CD) spectroscopy, both in electronic and vibrational range (ECD, VCD), in combination with quantum chemical calculations. For compound 2, the X-ray structure was available; thus, the ECD in the solid sta...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22773

    authors: Górecki M,Capozzi MAM,Albano G,Cardellicchio C,Di Bari L,Pescitelli G

    更新日期:2018-01-01 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

  • Plant and soil enantioselective biodegradation of racemic phenoxyalkanoic herbicides.

    abstract::The biodegradation of the chiral phenoxyalkanoic herbicides 2-(2,4-dichlorophenoxy)propionic aid (2,4-DP) and 2-(4-chloro-2-methylphenoxy)propionic acid (MCPP) was investigated using enantioselective HPLC and chiroptical detection. Racemic mixtures of 2,4-DP and MCPP were applied to three species of turf grass, four s...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1999)11:4<330::AID-CHIR12>

    authors: Schneiderheinze JM,Armstrong DW,Berthod A

    更新日期:1999-01-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10096

    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

  • 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

  • Absolute configuration and conformational analysis of a degradation product of inhalation anesthetic Sevoflurane: A vibrational circular dichroism study.

    abstract::1,1,1,3,3-pentafluoro-2-(fluoromethoxy)-3-methoxypropane, compound B, is a product obtained in the degradation of the anesthetic Sevoflurane. Enantiopure (+)-B was investigated using vibrational circular dichroism (VCD). Experimental absorption and VCD spectra of (+)-B in CDCl(3) solution in the 2,000-900 cm(-1) regio...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10106

    authors: Wang F,Polavarapu PL,Schurig V,Schmidt R

    更新日期:2002-08-01 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

  • Stereoselective determination of metoprolol and its metabolite α-hydroxymetoprolol in plasma by LC-MS/MS: application to pharmacokinetics during pregnancy.

    abstract::Metoprolol is available for clinical use as a racemic mixture. The S-(-)-metoprolol enantiomer is the one expressing higher activity in the blockade of the β(1)-adrenergic receptor. The α-hydroxymetoprolol metabolite also has activity in the blockade of the β(1)-adrenergic receptor. The present study describes the dev...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22102

    authors: Antunes Nde J,Cavalli RC,Marques MP,Lanchote VL

    更新日期:2013-01-01 00:00:00

  • High-Performance Liquid Chromatographic Enantioseparation of Cyclic β-Amino Acids on Zwitterionic Chiral Stationary Phases Based on Cinchona Alkaloids.

    abstract::Stereoselective high-performance liquid chromatographic separations of eight sterically constrained cyclic β-amino acid enantiomer pairs were carried out using the newly developed Cinchona alkaloid-based zwitterionic chiral stationary phases Chiralpak ZWIX(+) and ZWIX(-). The effects of the mobile phase composition, t...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22458

    authors: Ilisz I,Gecse Z,Lajkó G,Forró E,Fülöp F,Lindner W,Péter A

    更新日期:2015-09-01 00:00:00

  • Enantioselectivity of esterases in human brain.

    abstract::Subcellular fractions of three human brain specimens were found to contain esterase activities which hydrolyzed racemic oxazepam 3-acetate (rac-OXA). All three human brain preparations were highly selective toward the S-enantiomer of rac-OXA. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530050714

    authors: Yang SK,Huang A,Huang JD

    更新日期:1993-01-01 00:00:00

  • Enantioselectivity of inhibition of cytochrome P450 3A4 (CYP3A4) by ketoconazole: Testosterone and methadone as substrates.

    abstract::Racemic ketoconazole (KTZ) was the first orally active azole antifungal agent used in clinical practice and has become widely used in the treatment of mucosal fungal infections associated with AIDS immunosuppression and cancer chemotherapy. However, the use of KTZ has been limited because of adverse drug-drug interact...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10294

    authors: Dilmaghanian S,Gerber JG,Filler SG,Sanchez A,Gal J

    更新日期:2004-02-01 00:00:00

  • Asymmetric catalytic ene-cyclization approach to 2-fluoro-19-nor-1,25-dihydroxyvitamin D(3) A-ring analog with significant transactivation activity.

    abstract::1alpha,25-Dihydroxyvitamin D(3) (1alpha,25(OH)2D3) has been shown to modulate not only proliferation and differentiation, but also apoptosis in malignant cells, indicating that it could be useful for the treatment of cancer and psoriasis. However, little information has been available on the binding conformation of th...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.1046

    authors: Mikami K,Ohba S,Ohmura H,Kubodera N,Nakagawa K,Okano T

    更新日期:2001-07-01 00:00:00

  • Simultaneous Chiral Separation of Flavanone, Naringenin, and Hesperetin Enantiomers by RP-UHPLC-DAD.

    abstract::A rapid and effective RP-UHPLC-DAD method for enantioseparation of three flavanones, i.e., flavanone, naringenin, and hesperetin, was developed and validated. Chromatographic separation of the analytes was performed using a Chiralpak AD-3R analytical column under reverse phase conditions with methanol as the mobile ph...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22559

    authors: Baranowska I,Hejniak J,Magiera S

    更新日期:2016-02-01 00:00:00