Channel-like crystal structure of cinchoninium L-O-phosphoserine salt dihydrate.

Abstract:

:Studies on the interactions between L-O- phosphoserine, as one of the simplest fragments of membrane components, and the Cinchona alkaloid cinchonine, in the crystalline state were performed. Cinchoninium L-O-phosposerine salt dihydrate (PhSerCin) crystallizes in a monoclinic crystal system, space group P2(1), with unit cell parameters: a = 8.45400(10) A, b = 7.17100(10) A, c = 20.7760(4) A, alpha = 90 degrees , beta = 98.7830(10) degrees , gamma = 90 degrees , Z = 2. The asymmetric unit consists of the cinchoninium cation linked by hydrogen bonds to a phosphoserine anion and two water molecules. Intermolecular hydrogen bonds connecting phosphoserine anions via water molecules form chains extended along the b axis. Two such chains symmetrically related by twofold screw axis create a "channel." On both sides of this channel cinchonine cations are attached by hydrogen bonds in which the atoms N1, O12, and water molecules participate. This arrangement mimics the system of bilayer biological membrane.

journal_name

Chirality

journal_title

Chirality

authors

Wesełucha-Birczyńska A,Oleksyn BJ,Watroba J

doi

10.1002/chir.20784

subject

Has Abstract

pub_date

2010-06-01 00:00:00

pages

557-64

issue

6

eissn

0899-0042

issn

1520-636X

journal_volume

22

pub_type

杂志文章
  • Chemoselectivity issues of the asymmetric interaction between cyclohexanone, β-nitrostyrene, and benzoic acid under 5-aryl prolinate's organocatalysis.

    abstract::4-l-menthyloxycarbonyl 5-aryl prolinates were studied as organocatalysts of a novel three-component reaction of cyclohexanone, benzoic acid, and β-nitrostyrene. The presence of ortho-halogen atom in 5-aryl fragment of the catalyst is favored for driving the formation of chiral 7a-hydroxyoctahydro-2H-indol-2-one scaffo...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23212

    authors: Ivantcova PM,Kudryavtsev KV

    更新日期:2020-06-01 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

  • Stereoselective Behavior of the Chiral Herbicides Diclofop-Methyl and Diclofop During the Soy Sauce Brewing Process.

    abstract::Chiral pesticides are now receiving more and more attention in the food-making process. This experiment studied the enantioselective behavior of diclofop-methyl (DM) and its main metabolite, diclofop (DC), during the soy sauce brewing process. Two kinds of commonly used strains, Aspergillus oryzae and Saccharomyces ro...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22545

    authors: Lu Y,Zhang D,Liao Y,Diao J,Chen X

    更新日期:2016-01-01 00:00:00

  • Evaluation of the enantioselectivity of capillary electrokinetic chromatography using ethanediamine-bonded poly (glycidyl methacrylate) microspheres as the pseudostationary phases.

    abstract::In this work, a new capillary electrokinetic chromatography (EKC) approach using ethanediamine-bonded poly (glycidyl methacrylate) (Ami-PGMA) microspheres as pseudostationary phases (PSPs) for enantioseparation with a polysaccharide, chondroitin sulfate E (CSE), as the chiral selector. The CSE@Ami-PGMA EKC system was ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23035

    authors: Sun X,Yu T,Xu G,Du Y,Chen J,Li X

    更新日期:2019-02-01 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

  • 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

  • Research into the oxidation of abietic acid-derived enone with atmospheric oxygen.

    abstract::This work presents results of methyl 7-oxoabiet-13(14)-en-18-oate (3) self-oxidation with air-oxygen in the presence of various bases such as triethylamine or sodium t-butoxide. While under aerobic conditions, the use of sodium t-butoxide as a base results in the formation of four isomeric alcohols, an addition of tri...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23176

    authors: Masnyk M,Kuśmirek D,Trzybiński D,Frelek J

    更新日期:2020-04-01 00:00:00

  • In vitro stereoselective degradation of carprofen glucuronide by human serum albumin. Characterization of sites and reactive amino acids.

    abstract::Acyl glucuronides formed from carboxylic acids can undergo hydrolysis, acyl migration, and covalent binding to proteins. In buffers at physiological pH, the degradation of acylglucuronide of a chiral NSAID, carprofen, consisted mainly of acyl migration. Acidic pH reduced hydrolysis and acyl migration, thus stabilizing...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(2000)12:2<53::AID-CHIR1>3.

    authors: Georges H,Presle N,Buronfosse T,Fournel-Gigleux S,Netter P,Magdalou J,Lapicque F

    更新日期:2000-02-01 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

  • 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 chiral analysis of amphetamine-type stimulants and ephedrine by capillary electrophoresis coupled to time-of-flight mass spectrometry.

    abstract::This study focused on the chiral characteristics of methamphetamine seizures in Shanghai for inferring the synthetic pathways of drugs. Capillary electrophoresis coupled to time-of-flight mass spectrometry was used for simultaneous chiral separation of amphetamine-type stimulants and ephedrine, including S(+)-amphetam...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22987

    authors: Cui X,Liang C,Gong F,Wang R,Ni C,Wu Y,Chen G,Zhang Y

    更新日期:2018-09-01 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

  • Utilizing hydrolases of opposite enantiopreference for the preparation of both enantiomers of (1R,7aR)-(-)- and (1S,7aS)-(+)-3,6,7,7a-tetrahydro-1-hydroxy-7a-methyl-1H-inden-5(2H)-one.

    abstract::Four racemic esters of (1R*,7aR*)-3,6,7,7a-tetrahydro-1-hydroxy-7a-methyl-1H-inden-5(2H)-one were prepared and subjected to hydrolysis with two types of hydrolases, including alcalase and three lipases. Alcalase and lipase showed opposite enantiopreference on these esters. Based on this result, we developed a gram-sca...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20023

    authors: Lo LC,Chou TC,Shie JJ

    更新日期:2004-05-05 00:00:00

  • Chiroptical properties of 2,2'-bioxirane.

    abstract::The two enantiomers of 2,2'-bioxirane were synthesized, and their chiroptical properties were thoroughly investigated in various solvents by polarimetry, vibrational circular dichroism (VCD), and Raman optical activity (ROA). Density functional theory (DFT) calculations at the B3LYP/aug-cc-pVTZ level revealed the pres...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22814

    authors: Daugey N,De Rycke N,Brotin T,Buffeteau T

    更新日期:2018-04-01 00:00:00

  • The so-called "interconversion" of stereoisomeric drugs: an attempt at clarification.

    abstract::A variety of reactions can be categorized under the global concept of the "interconversion of stereoisomers." Thus, racemization or epimerization can result from inversion of labile chiral centers. From the examples available, some predictive rules are suggested for a chiral center of the type R"R'RC-H undergoing base...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.530050302

    authors: Testa B,Carrupt PA,Gal J

    更新日期:1993-01-01 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

  • 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

  • A Simple ¹³C NMR Method for the Discrimination of Complex Mixtures of Stereoisomers: All Eight Stereoisomers of α-Tocopherol Resolved.

    abstract::A simple one-dimensional (13)C NMR method is presented to discriminate between stereoisomers of organic compounds with more than one chiral center. By means of this method it is possible to discriminate between all eight stereoisomers of α-tocopherol. To achieve this the chiral solvating agent (S)-(+)-1-(9-anthryl)-2,...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22535

    authors: Lankhorst PP,Netscher T,Duchateau AL

    更新日期:2015-11-01 00:00:00

  • Effect of the mobile phase on the retention behavior of optical isomers of the mandelic acid derivative methyl 2-phenyl-2-(tetrahydropyranyloxy) acetate by chiral HPLC.

    abstract::Conditions for separation of enantiomers of a mandelic acid derivative, methyl 2-phenyl-2-(tetrahydropyranyloxy) acetate (the analyte) were studied. Because of the presence of two chiral carbons, the analyte consists of four stereoisomers stable at ambient temperature. Chiral HPLC of the analyte resulted in four peaks...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20304

    authors: Shen B,Xu X,Chen J,Zhang X,Xu B

    更新日期:2006-09-01 00:00:00

  • Separation of amino acid enantiomers by micelle-enhanced ultrafiltration.

    abstract::A Micelle-enhanced ultrafiltration (MEUF) separation process was investigated that can potentially be used for large-scale enantioseparations. Copper(II)-amino acid derivatives dissolved in nonionic surfactant micelles were used as chiral selectors for the separation of dilute racemic amino acids solutions. For the al...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/1520-636X(2000)12:8<627::AID-CHIR5>3.0.CO;

    authors: De Bruin TJ,Marcelis AT,Zuilhof H,Rodenburg LM,Niederländer HA,Koudijs A,Overdevest PE,Van der Padt A,Sudhölter EJ

    更新日期:2000-08-01 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

  • Chiral investigation of midodrine, a long-acting alpha-adrenergic stimulating agent.

    abstract::Midodrine hydrochloride is a peripheral alpha(1)-adrenoreceptor agonist that induces venous and arterial vasoconstriction. Midodrine, after oral or intravenous administration, undergoes enzymatic hydrolysis and releases deglymidodrine, a pharmacologically active metabolite. Midodrine and deglymidodrine have a chiral c...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20041

    authors: Quaglia MG,Farina A,Palmery M,Desideri N,Donati E,Bossù E,Strano S

    更新日期:2004-07-01 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

  • 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

  • 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

  • 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

  • Chiral 1,1'-binaphthyl-2,2'-dithiol-stabilized gold clusters: size separation and optical activity in the UV-vis.

    abstract::Gold particles covered with 1,1'-binaphthyl-2,2'-dithiol (BINAS) were prepared. Using size exclusion chromatography, it was possible for the first time to separate the sample into fractions with different sizes and colors. Transmission electron microscopy shows that the particles are very small, in the order of 1 nm o...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20488

    authors: Gautier C,Taras R,Gladiali S,Bürgi T

    更新日期:2008-03-01 00:00:00

  • Enantiospecific analysis of 8-prenylnaringenin in biological fluids by liquid-chromatography-electrospray ionization mass spectrometry: application to preclinical pharmacokinetic investigations.

    abstract::8-Prenylnaringenin (8PN) is a naturally occurring bioactive chiral prenylflavonoid found most commonly in the female flowers of hops (Humulus lupulus L.). A stereospecific method of analysis for 8PN in biological fluids is necessary to study the pharmacokinetic disposition of each enantiomer. A novel and simple liquid...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22343

    authors: Martinez SE,Lakowski TM,Davies NM

    更新日期:2014-08-01 00:00:00

  • Molecular enantiorecognition of l-glucose and d-glucose in whole blood samples.

    abstract::In the past years, enantioanalysis became very important for clinical analysis; biomarkers/substances of biomedical importance with chiral structure should be analyzed and their presence correlated with the specific disorder. Therefore, we developed a method for the assay of l- and d-glucose, based on molecular recogn...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22843

    authors: Stefan-van Staden RI,Mitrofan G

    更新日期:2018-05-01 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