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 methylene bridging carbons. The synthetic background and general physical and chemical properties of the Q[n] as molecular hosts is discussed. Particular attention is drawn to the synthesis of structural variants that have significance for chiral recognition properties such as (±)-bis-nor-seco-Q[6] and (±)-bis-nor-seco-Q[10]. Furthermore, examples of chiral recognition, enantio- and stereoselectivity using the achiral Q[n] as supramolecular structures with a chiral function directly or indirectly via another chiral agent are also discussed.

journal_name

Chirality

journal_title

Chirality

authors

Mandadapu V,Day AI,Ghanem A

doi

10.1002/chir.22363

subject

Has Abstract

pub_date

2014-11-01 00:00:00

pages

712-23

issue

11

eissn

0899-0042

issn

1520-636X

journal_volume

26

pub_type

杂志文章,评审
  • Resolution of enantiomers of novel C2 -symmetric aminobisphosphinic acids via diastereomeric salt formation with quinine.

    abstract::C2 -symmetric N,N-bis(phosphinomethyl)amines were prepared by the thermal reaction of aromatic aldehydes with ammonia and hypophosphorus acid as previously described. Both enantiomers of C2 -symmetric N,N-bis(phosphinomethyl)amine were obtained in a high enantiomeric purity through the diastereomeric salt formation wi...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22391

    authors: Kaboudin B,Faghihi MR,Kazemi F,Yokomatsu T

    更新日期:2015-01-01 00:00:00

  • The enantioselective enrichment, metabolism, and toxicity of fenoxaprop-ethyl and its metabolites in zebrafish.

    abstract::To investigate the impacts of the widely used chiral herbicide fenoxaprop-ethyl (FE) on aquatic organisms, the enrichment, metabolism, acute toxicity, and oxidative stress of fenoxaprop-ethyl and its main metabolites fenoxaprop (FA), ethyl-2-(4-hydroxyphenoxy)propanoate (EHPP), 2-(4-hydroxyphenoxy)propanoic acid (HPPA...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23222

    authors: Xu Y,Jing X,Zhai W,Li X

    更新日期:2020-07-01 00:00:00

  • Improvement of enantioselective syntheses and chiral high resolution gas chromatographic analyses of (+)-2-allyl-2-carboethoxy-cyclopentanol.

    abstract::The improvement of the biocatalytic reduction of 2-allyl-carboethoxy-cyclopentanone (2) to the corresponding cyclopentanol derivative (+)-(1R,2R)-(1) was accomplished employing baker's yeast in organic media. This chiral cyclopentanol derivative (1), analyzed by high resolution gas chromatography performed over beta-c...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1997)9:4<321::AID-CHIR1>3.

    authors: Fraga CA,Barreiro EJ,da Silva EF,dos Santos AR,KV Ramos MdaC,de Aquino Neto FR

    更新日期:1997-01-01 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

  • An integrating sphere to measure CD from difficult samples

    abstract::Integrating spheres are widely used with UV-Vis and occasionally with infrared spectrophotometers to measure different types of samples, either in transmission mode (scattered transmission accessories) or in total/diffuse reflectance mode. We built a prototype sphere of the demountable type, which fits easily the samp...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(2000)12:4<291::AID-CHIR16>

    authors: Castiglioni E,Albertini P

    更新日期:2000-05-01 00:00:00

  • (R,R)-N,N'-dimethylcyclohexyl-1,2-diazaseleno-phospholidine as a chiral derivatizing agent for the evaluation of chiral alcohols.

    abstract::Previously, a diazaphospholidine has been synthesized and evaluated as a chiral derivatizing reagent for the determination of the optical purity of chiral alcohols via 31P NMR spectroscopy (Alexakis et al., J. Org. Chem. 57:1224-1237, 1992). Our laboratory is interested in the advantageous and practical applications o...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530060306

    authors: House KL,O'Connor MJ,Silks LA 3rd,Dunlap RB,Odom JD

    更新日期:1994-01-01 00:00:00

  • Asymmetric aldol reactions catalyzed by efficient and recyclable silica-supported proline-based peptides.

    abstract::A series of silica-supported proline-based peptides were synthesized and applied as catalysts for direct asymmetric intermolecular aldol reactions. Among these, a peptide with two L-proline units was found to be the most efficient one for the asymmetric aldol reactions between acetone and aromatic aldehydes. The react...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20603

    authors: Yan J,Wang L

    更新日期:2009-04-01 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

  • Time-resolved circularly polarized luminescence of Eu3+ -based systems.

    abstract::Chiral Eu3+ -based systems are frequently studied via circularly polarized luminescence spectroscopy. The emission lifetimes of each circular polarization, however, are virtually always ignored, because in a homogeneous sample of emitters, there should be no difference between the two. However, we show that in less ro...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23293

    authors: Hananel U,Schwartz G,Paiss G,Arrico L,Zinna F,Di Bari L,Cheshnovsky O,Markovich G

    更新日期:2020-12-30 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

  • 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

  • Asymmetric Diels-Alder reaction involving chiral benzimidazoles as organocatalysts.

    abstract::(S)-(-)-2-(α-hydroxyethyl)-benzimidazole and (S)-(+)-2-(α-hydroxybenzyl)-benzimidazole work as chiral Brønsted bases (BBs) in Diels-Alder reaction between anthrone and maleimides under mild reaction condition. These chiral BBs cause asymmetric induction. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20942

    authors: Mirgane NA,Karnik AV

    更新日期:2011-05-01 00:00:00

  • New atropisomeric amino alcohol ligands for enantioselective addition of diethylzinc to aldehydes.

    abstract::Efficient synthesis of several new atropisomeric amino alcohols having 1-phenyl-1H-pyrrole skeleton are reported. Steric arrangements of the products were confirmed by a single-crystal X-ray measurement. The consequences of the size of the N-substituents on enantioinduction were examined by employing the enantioselect...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22415

    authors: Faigl F,Deák S,Erdélyi Z,Holczbauer T,Czugler M,Nyerges M,Mátravölgyi B

    更新日期:2015-03-01 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

  • Circular dichroism eigenspectra of polyproline II and β-strand conformers of trialanine in water: Singular value decomposition analysis.

    abstract::Despite that a number of experimental and theoretical investigations have been carried out to determine the structure of trialanine in water, the reported populations of polyproline II (PPII) and β-strand conformers vary and were found to be dependent on which spectroscopic method was used. Such discrepancies are due ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20870

    authors: Oh KI,Lee KK,Park EK,Yoo DG,Hwang GS,Cho M

    更新日期:2010-01-01 00:00:00

  • Polarization in France.

    abstract::The special relationship between France and the polarization of light from the beginning of the 19th century until the present day is reviewed in the lives and works of Étienne Louis Malus, François Arago, Jean-Baptiste Biot, Augustin Fresnel, Louis Pasteur, Frédéric Wallerant, Aimé Cotton, Francis Perrin, and Alain A...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22818

    authors: Kahr B

    更新日期:2018-04-01 00:00:00

  • Successful use of a novel lux® i-Amylose-1 chiral column for enantioseparation of "legal highs" by HPLC.

    abstract::Bath salts, fumigations, cleaners and air fresheners, behind these terms substances are hidden, which count as "Legal Highs". These fancy names are used to pretend Legal Highs as harmless compounds, to circumvent legal regulations for marketing as well as to increase the sales. Besides classic illicit drugs of synthet...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23135

    authors: Kadkhodaei K,Kadisch M,Schmid MG

    更新日期:2020-01-01 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

  • Comparison of mid-infrared Fourier transform vibrational circular dichroism measurements with single and dual polarization modulations.

    abstract::Fourier transform infrared vibrational circular dichroism (FTIR-VCD) measurements have gone through major advances in the last decade. A major thrust in these advances was to find ways that can minimize the VCD spectral artifacts and obtain the VCD signals at enhanced signal quality. However, all these advances are no...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20999

    authors: Polavarapu PL,Shanmugam G

    更新日期:2011-10-01 00:00:00

  • Supramolecular photochirogenesis with novel cyclic tetrasaccharide: enantiodifferentiating photoisomerization of (Z)-cyclooctene with cyclic nigerosylnigerose-based sensitizers.

    abstract::Isophthalic and terephthalic acid monoesters of cyclic nigerosyl-(1→6)-nigerose (CNN), a cyclic tetrasaccharide composed of four d-glucopyranosyl residues connected by alternating α-1,3- and α-1,6-linkages, were synthesized as novel chiral supramolecular sensitizers for enantiodifferentiating photoisomerization of (Z)...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22014

    authors: Yang C,Liang W,Nishijima M,Fukuhara G,Mori T,Hiramatsu H,Dan-oh Y,Tsujimoto K,Inoue Y

    更新日期:2012-11-01 00:00:00

  • A stereodynamic fluorescent probe for amino acids. Circular dichroism and circularly polarized luminescence analysis.

    abstract::The use of stereodynamic probes is becoming one of the leading strategies for the fast and effective determination of enantiomeric excess. Recently, we reported a series of novel molecular architectures based on a modified tris(2-pyridylmethyl)amine complex (TPMA), which are able to amplify the electronic CD, in the c...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22780

    authors: Carmo Dos Santos NA,Badetti E,Licini G,Abbate S,Longhi G,Zonta C

    更新日期:2018-01-01 00:00:00

  • C3-symmetrical self-assembled structures investigated by vibrational circular dichroism.

    abstract::We demonstrate by using vibrational circular dichroism (VCD) spectroscopy that it is possible to investigate the chirality of a supramolecular polymeric system in relatively dilute solutions. Chiral C(3)-symmetrical discotic molecules, based on a trialkylbenzene-1,3,5-carboxamide, form supramolecular columnar stacks w...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20568

    authors: Smulders MM,Buffeteau T,Cavagnat D,Wolffs M,Schenning AP,Meijer EW

    更新日期:2008-09-01 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

  • 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

  • Structural Basis and Mechanism of Chiral Benzedrine Molecules Interacting With Third Dopamine Receptor.

    abstract::In order to investigate the chiral benzedrine molecules corresponding to their different characteristics in biochemical systems, we studied their interaction with D3 R using the docking method, molecular dynamic simulation, and quantum chemistry. The obtained results indicate that the active residues for R-benzedrine ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22630

    authors: Wang M,Xie W,Li A,Xu S

    更新日期:2016-10-01 00:00:00

  • Determination of the absolute configuration and solution conformation of a novel disubstituted pyrrolidine acid A by vibrational circular dichroism.

    abstract::Compound A, a novel disubstituted pyrrolidine acid, is a member of a new class of agents that are potentially useful for the treatment of diabetes and dyslipidemia. The absolute configuration of this compound was determined by using vibrational circular dichroism (VCD). The results are in agreement with the assignment...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20316

    authors: Freedman TB,Cao X,Phillips LM,Cheng PT,Dalterio R,Shu YZ,Zhang H,Zhao N,Shukla RB,Tymiak A,Gozo SK,Nafie LA,Gougoutas JZ

    更新日期:2006-09-01 00:00:00

  • Improved synthesis and pharmacologic activity of the enantiomers of a new benzofurane type antiarrhythmic compound.

    abstract::An improved synthesis of the enantiomers of the new benzofurane-type antiarrhythmic compound 1 is described, which makes use of the enantiomerically pure mbe-lactol. Thus, acylation of the benzofurane 4 with acetic anhydride and subsequent bromination gave the bromoacetyl-derivative 6, which, after reduction with LiAl...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530060417

    authors: Ecker G,Fleischhacker W,Helml T,Noe CR,Scasny S,Lemmens-Gruber R,Studenik C,Marei H,Heistracher P

    更新日期:1994-01-01 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

  • 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

  • Highly diastereoselective addition of silyldihalomethyllithiums to chiral alkyl esters.

    abstract::Treatment of benzoate, formate, or trifluoroacetate esters with silyldibromomethyllithiums provides alkyl silyl mixed acetals via the 1,3-rearrangement of a silyl group from carbon to oxygen. A high level of asymmetric induction onto the acetal carbon is observed when chiral alkyl esters are employed. The stereochemic...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10152

    authors: Shinokubo H,Kondo J,Inoue A,Oshima K

    更新日期:2003-01-01 00:00:00