Measurements of concentration dependence and enantiomeric purity of terpene solutions as a test of a new commercial VCD spectrometer

Abstract:

:Vibrational circular dichroism (VCD) spectra of (+)-alpha-pinene solutions in carbon tetrachloride have been measured in the range of volume fractions 5-100% (v/v) in the mid-infrared region. The concentration dependence measured was statistically analyzed with the aim of obtaining a reliable correlation between the VCD band areas and the concentrations of individual enantiomers. The quality of the spectra was estimated by means of noise spectra which were defined as half the difference of the two following blocks of scans. In addition to this, the enantiomeric purity was studied. This study was carried out for both (+)- and (-)-alpha-pinene enantiomers in the range of the percent enantiomeric excess in the interval 10-100%. The relationship between VCD intensity and enantiomeric purity was determined by least-square regression and statistically evaluated. All measurements performed in this study were intended as a basic tool for testing of a new commercial VCD setup from Bruker. Copyright 2000 Wiley-Liss, Inc.

journal_name

Chirality

journal_title

Chirality

authors

Urbanova M,Setnicka V V,Volka K

doi

10.1002/(SICI)1520-636X(2000)12:4<199::AID-CHIR6>3

subject

Has Abstract

pub_date

2000-05-01 00:00:00

pages

199-203

issue

4

eissn

0899-0042

issn

1520-636X

pii

10.1002/(SICI)1520-636X(2000)12:4<199::AID-CHIR6>3

journal_volume

12

pub_type

杂志文章
  • 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

  • Circular dichroism and the interactions of water soluble porphyrins with DNA.

    abstract::The size, sign, and profile of induced circular dichroism (CD) features in the Soret region are reliable indicators of the binding modes of porphyrins and metalloporphyrins to DNA. Porphyrins shown (using such CD criteria) to be intercalators in monodispersed DNA duplexes prove extremely useful for the detection and c...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.10206

    authors: Pasternack RF

    更新日期:2003-05-05 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

  • Configuration of heptopyranoside and heptofuranoside side chains: 2-anthroate, a powerful chromophore for exciton coupled CD.

    abstract::The absolute configuration of the acyclic side chain of heptopyranosides and heptofuranosides was determined by exciton coupled CD, employing the strongly fluorescent 2-anthroate chromophore. The usage of this chromophore offers significant improvements over previous chemical and spectroscopic procedures since its int...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1997)9:7<699::AID-CHIR11>3

    authors: Akritopoulou-Zanze I,Nakanishi K,Stepowska H,Grzeszczyk B,Zamojski A,Berova N

    更新日期:1997-01-01 00:00:00

  • Theoretical Modeling of Surface Confined Chiral Nanoporous Networks: Cruciform Molecules as Versatile Building Blocks.

    abstract::Patterning of solid surfaces with functional organic molecules has been a convenient route to fabricate two-dimensional materials with programmed architecture and activities. One example is the chiral nanoporous networks that can be created via controlled self-assembly of star-shaped molecules under 2D confinement. In...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22437

    authors: Kasperski A,Szabelski P

    更新日期:2015-07-01 00:00:00

  • A new definition of life.

    abstract::Chirality is often glossed over in theoretical or experimental discussions concerning the origin of life, but the ubiquity of homochiral building blocks in known biological systems demands explanation. Information theory can provide a quantitative framework for understanding the role of chirality in biology. Here I sh...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20590

    authors: Carroll JD

    更新日期:2009-03-01 00:00:00

  • Rationalization of the multireceptorial character of chiral solvating agents based on quinine and its derivatives: overview of selected NMR investigations.

    abstract::A summary of selected NMR studies of enantiodiscrimination phenomena regarding the use of quinine-based chiral solvating agents (CSAs) for the determination of the enantiomeric compositions in solution is reported, with explanations of their multireceptorial character offered. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20134

    authors: Uccello-Barretta G,Balzano F,Salvadori P

    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

  • Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism.

    abstract::Advances in the measurement, calculation, and application of vibrational circular dichroism (VCD) for the determination of absolute configuration are described. The purpose of the review is to provide an up-to-date perspective on the capability of VCD to solve problems of absolute stereochemistry for chiral molecules ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10287

    authors: Freedman TB,Cao X,Dukor RK,Nafie LA

    更新日期:2003-11-01 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

  • 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

  • How do reaction conditions affect the enantiopure synthesis of 2-substituted-1,4-benzodioxane derivatives?

    abstract::Several biologically active compounds structurally include the enantiopure 2-substituted-1,4-benzodioxane scaffold. The straightforward racemization that affects reactions involving most of the common chemical reactives is thus a crucial issue. The developing of a completely stereo-controlled synthetic route that does...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22968

    authors: Straniero V,Casiraghi A,Fumagalli L,Valoti E

    更新日期:2018-07-01 00:00:00

  • Chiroptical studies on supramolecular chirality of molecular aggregates.

    abstract::The attempts of applying chiroptical spectroscopy to supramolecular chirality are reviewed with a focus on vibrational circular dichroism (VCD). Examples were taken from gels, solids, and monolayers formed by low-molecular mass weight chiral gelators. Particular attention was paid to a group of gelators with perfluoro...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.22482

    authors: Sato H,Yajima T,Yamagishi A

    更新日期:2015-10-01 00:00:00

  • A Solid Phase Vibrational Circular Dichroism Study of Polypeptide-Surfactant Interaction.

    abstract::We studied the interaction of poly-l-lysine (PLL) and poly-l-arginine (PLAG) with sodium dodecyl sulfate (SDS) surfactant and the interaction of poly-l-glutamic acid (PLGA) and poly-l-aspartic acid (PLAA) with tetradecyltrimethylammonium bromide (TTAB) surfactant using vibrational circular dichroism (VCD) spectroscopy...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22534

    authors: Novotná P,Urbanová M

    更新日期:2015-12-01 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

  • Dynorphin A analogs containing a conformationally constrained phenylalanine derivative in position 4: reversal of preferred stereochemistry for opioid receptor affinity and discrimination of kappa vs. delta receptors.

    abstract::Analogs of the opioid peptide [D-Ala8]dynorphin A-(1-11)NH2 containing optically pure (R)- and (S)-2-aminotetralin-2-carboxylic acid (Atc) in position 4 were synthesized and evaluated for opioid receptor affinity. These peptides are the first reported dynorphin A analogs containing a conformationally constrained amino...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/1520-636X(2001)13:3<125::AID-CHIR1008>3.0.

    authors: Aldrich JV,Zheng QI,Murray TF

    更新日期:2001-01-01 00:00:00

  • 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

  • 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

  • Stereoselective pharmacokinetics of (R)-(+)- and (S)-(-)-rabeprazole in human using chiral LC-MS/MS after administration of rabeprazole sodium enteric-coated tablet.

    abstract::Rabeprazole is an effective proton pump inhibitor to treat acid-related diseases. To achieve the simultaneous determination of rabeprazole enantiomers in human plasma, a chiral LC-MS/MS method was developed and validated. Acetonitrile including 0.1% ammonium were used as protein precipitating agent. Analytes were sepa...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23022

    authors: Sun LN,Shen YW,Ying YW,Li D,Li TF,Zhang XH,Zhao P,Ding L,Wang YQ

    更新日期:2018-12-01 00:00:00

  • Enantioselective LC/MS method for the determination of an antimalarial agent Fenozan B07 in dog plasma.

    abstract::A chiral liquid chromatography/mass spectrometry (LC/MS) bioanalytical procedure has been developed for the analysis of the antimalaric agent Fenozan B07 in dog plasma. Normal-phase chromatography involving a phenylcarbamate derivative of cellulose coated on silica gel as the chiral stationary phase was used to resolv...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20253

    authors: Maraschiello C,Vilageliu J,Dorronsoro I,Martinez A,Floriano P,Gómez-Acebo E

    更新日期:2006-05-15 00:00:00

  • Variable stereochemistry in highly branched isoprenoids from diatoms.

    abstract::C(25) highly branched isoprenoid (HBI) alkenes are ubiquitous lipids found in geochemical samples around the globe. The origins of these widespread geochemicals are believed to be restricted to a limited number of diatoms, including Haslea ostrearia (and related species), Rhizosolenia setigera, and Pleurosigma interme...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.1053

    authors: Belt ST,Allard WG,Johns L,König WA,Massé G,Robert JM,Rowland S

    更新日期:2001-08-01 00:00:00

  • Synthesis and characterization of conformationally rigid chiral pyridine-N-heterocyclic carbene-based palladacycles with an unexpected Pd-N bond cleavage.

    abstract::The versatility of a previously developed method for the synthesis of chiral carbene-based palladacycles is demonstrated through the synthesis of two new chiral pyridine-functionalized N-heterocyclic carbene palladacycles with different wingtip groups. The efficiency in their resolution with different counter anions a...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22116

    authors: Ng KH,Li Y,Tan WX,Chiang M,Pullarkat SA

    更新日期:2013-03-01 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

  • Effect of serum lipoproteins on stereoselective halofantrine metabolism by rat hepatocytes.

    abstract::Experimental hyperlipidemia has shown to decrease cytochrome P450 3A4 and 2C11 expression and to increase liver concentrations and the plasma protein binding of halofantrine (HF) enantiomers. The present study examined the effect of hyperlipidemic (HL) serum on the metabolism of HF enantiomers by primary rat hepatocyt...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22054

    authors: Patel JP,Hamdy DA,El-Kadi AO,Brocks DR

    更新日期:2012-07-01 00:00:00

  • Headspace gas chromatography-mass spectrometry analysis of isoflurane enantiomers in blood samples after anesthesia with the racemic mixture.

    abstract::Several in vivo and in vitro studies on the stereoselective potency of isoflurane enantiomers suggest beneficial effects of the (+)-(S)-enantiomer. In order to detect possible differences in the pharmacokinetics of isoflurane enantiomers, a clinical study of 41 patients undergoing general anesthesia maintained with ra...

    journal_title:Chirality

    pub_type: 临床试验,杂志文章

    doi:10.1002/(SICI)1520-636X(1999)11:3<206::AID-CHIR6>3

    authors: Schmidt R,Wahl HG,Häberle H,Dieterich HJ,Schurig V

    更新日期:1999-01-01 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

  • 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

  • NMR chiral discrimination of chalcogen containing secondary alcohols.

    abstract::Here, we report the general strategies by which NMR spectroscopy can be used to determine the enantiopurity and absolute configuration of chalcogen containing secondary alcohols, including the evaluation of the use of chiral solvating and chiral derivatizing agents. The BINOL/DMAP ternary complex demonstrated a simple...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23030

    authors: Marques NBG,Jacob RG,Perin G,Lenardão EJ,Alves D,Silva MS

    更新日期:2019-01-01 00:00:00

  • Cucurbituril: chiral applications.

    abstract::This review brings together the past and current methods for synthesizing the classical cucurbit[n]uril (Q[n]), structural variants, and derivatives. Here we refer to the first family of Q[n] as " classical," where the cavity is spheroidal and carry no substituents at any of the equatorial methine carbons or the methy...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.22363

    authors: Mandadapu V,Day AI,Ghanem A

    更新日期:2014-11-01 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