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 scales. Here, we report that enantiomerically pure helices with micron scale of chirality can be assembled on Campylobacter jejuni, a helical bacterium known for severe stomach infections. These organisms have right-handed helical shapes with a pitch of 1-2 microns and can serve as versatile templates for a variety of NPs. The bacteria itself shows no observable rotatory activity in the visible, red, and near-IR ranges of electromagnetic spectrum. The bacterial dispersion acquires chiroptical activity at 500-750 nm upon plasmonic functionalization with Au NPs. Finite-difference time-domain simulations confirmed the attribution of the chiroptical activity to the helical assembly of gold nanoparticles. The position of the circular dichroism peaks observed for these chiral structures overlaps with those obtained before for Au NPs and their constructs with molecular and nanoscale chirality. This work provides an experimental and computational pathway to utilize chiroplasmonic particles assembled on bacteria for bioanalytical purposes.

journal_name

Chirality

journal_title

Chirality

authors

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

doi

10.1002/chir.23225

subject

Has Abstract

pub_date

2020-07-01 00:00:00

pages

899-906

issue

7

eissn

0899-0042

issn

1520-636X

journal_volume

32

pub_type

杂志文章
  • 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

  • Modulatory effect of chiral nonsteroidal anti-inflammatory drugs on apoptosis of human neutrophils.

    abstract::Polymorphonuclear neutrophils (PMNs) are short-lived leukocytes that die by apoptosis. Although PMNs are crucial in the defense against infection, they have been implicated in the pathogenesis of tissue injury observed in inflammatory diseases. The induction or prevention of PMN apoptosis is currently discussed as a k...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20516

    authors: Zielińska-Przyjemska M,Główka FK,Klaczyńska J

    更新日期:2008-02-01 00:00:00

  • Synthesis of epimers of L-cyclopentenylglycine using enzymatic resolution.

    abstract::Both epimers of the naturally occurring nonproteinogenic amino acid L-cyclopentenylglycine, (2S,1'S)- and (2S, 1'R)-2-(cyclopent-2'-enyl)glycine, were obtained via a procedure involving condensation of 3-chlorocyclopentene with diethyl acetylaminomalonate, deethoxycarbonylation, chromatographic separation of the resul...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/1520-636X(2000)12:9<665::AID-CHIR4>3.0.CO;

    authors: Andersen L,Nielsen B,Jaroszewski JW

    更新日期:2000-10-01 00:00:00

  • Enantioselective separation and degradation of the herbicide dichlorprop methyl in sediment.

    abstract::Chiral pesticides currently constitute about 50% of all pesticides dosage used in China, and this ratio is increasing as more complex structures are introduced. Dichlorprop methyl (DCPPM) is a chiral herbicide consisting of a pair of enantiomers. In this study, the enantiomeric separation of DCPPM was investigated by ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20624

    authors: Ma Y,Xu C,Wen Y,Liu W

    更新日期:2009-04-01 00:00:00

  • Synthesis of Novel Chiral Sulfonamide-Bearing 1,2,4-Triazole-3-thione Analogs Derived from D- and L-Phenylalanine Esters as Potential Anti-Influenza Agents.

    abstract::Novel enantiopure 1,2,4-trizole-3-thiones containing a benzensulfonamide moiety were synthesized via multistep reaction sequence starting with D-phenylalanine methyl ester and L-phenylalanine ethyl ester as a source of chirality. The chemical structures of all compounds were characterized by elemental analysis, UV, IR...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22607

    authors: Başaran E,Karaküçük-Iyidoğan A,Schols D,Oruç-Emre EE

    更新日期:2016-06-01 00:00:00

  • Cyclodextrin-Functionalized Monolithic Capillary Columns: Preparation and Chiral Applications.

    abstract::In this review, the recently reported approaches for the preparation of cyclodextrin-functionalized capillary monolithic columns are highlighted, with few applications in chiral separations using capillary liquid chromatography (CLC) and capillary electrochromatography (CEC). Chirality 28:97-109, 2016. © 2015 Wiley Pe...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.22550

    authors: Adly FG,Antwi NY,Ghanem A

    更新日期:2016-02-01 00:00:00

  • Evaluation of the enantiomeric composition of amino acids in tobacco.

    abstract::Despite the fact that several studies have reported the concentrations of various free amino acids in tobacco, their enantiomeric composition is unknown. Both the absolute and enantiomeric compositions of proline, alanine, asparagine, aspartic acid, valine, methionine, leucine,and phenylalanine were determined for thr...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1999)11:8<669::AID-CHIR10>

    authors: Kullman JP,Chen X,Armstrong DW

    更新日期:1999-01-01 00:00:00

  • Synthesis of novel chiral metal complexes derived from chiral thiosemicarbazide ligands as potential antioxidant agents.

    abstract::Two new chiral thiosemicarbazide ligands and their Cu (II), Ni (II), Pd (II), and Zn (II) complexes were synthesized and characterized by nuclear magnetic resonance (NMR) (only for ligand), Fourier transform infrared (FT-IR), ultraviolet visible (UV-Vis), mass, and elemental analysis. The antioxidant activity of ligan...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23069

    authors: Başaran E,Sıcak Y,Sogukomerogullari HG,Karaküçük-Iyidoğan A,Oruç-Emre EE,Sönmez M,Öztürk M

    更新日期:2019-06-01 00:00:00

  • Unexpected rearrangement of enantiomerically pure 3-aminoquinuclidine as a simple way of preparing diastereomeric octahydropyrrolo[2,3-c]pyridine derivatives.

    abstract::Reaction of (S)- or (R)-3-aminoquinuclidine with 2-chloropyrimidine or 2-bromopyrimidine led to an unexpected formation of both cis- and trans-octahydropyrrolo [2,3]pyridine derivatives. A single-step synthesis of two of the four stereoisomers of these octahydropyrrolo[2,3]pyridine derivatives provides a convenient wa...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20663

    authors: Goljer I,Molinari A,He Y,Nogle L,Sun W,Campbell B,McConnell O

    更新日期:2009-07-01 00:00:00

  • Capillary electrophoresis of herbicides. III. Evaluation of octylmaltopyranoside chiral surfactant in the enantiomeric separation of phenoxy acid herbicides.

    abstract::A chiral alkylglucoside surfactant, namely n-octyl-beta-D-maltopyranoside (OM), was evaluated in the enantiomeric separation of phenoxy acid herbicides. The enantiomeric resolution of the phenoxy acid herbicides could be manipulated readily by adjusting the surfactant concentration, ionic strength, pH, the percent org...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1996)8:7<518::AID-CHIR9>3.

    authors: Mechref Y,el Rassi Z

    更新日期:1996-01-01 00:00:00

  • 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 isoster...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530040807

    authors: Valente EJ,Zubkowski J,Eggleston DS

    更新日期:1992-01-01 00:00:00

  • Asymmetric reduction of β-ketoesters and chiral β-iminoesters: impact of a α-quaternary stereocenter.

    abstract::Diastereomeric reduction of nonactivated, hindered β-keto and chiral β-iminoesters are described. The influence of a α-stereocontrolled center on the efficiency and stereoselectivity of the reduction was studied. Reaction conditions were optimized to synthesize β-hydroxy- and β-aminoesters in good yields. In the case ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20909

    authors: Almahli H,Hendra F,Troufflard C,Cavé C,Joseph D,Delarue-Cochin S

    更新日期:2011-03-01 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

  • 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 mechan...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20212

    authors: Lynam KG,Stringham RW

    更新日期:2006-01-01 00:00:00

  • Enantioselective Friedel-Crafts reaction of indoles with trifluoroacetaldehyde catalyzed by Cinchona alkaloids.

    abstract::The first direct asymmetric synthetic preparation of trifluoro-1-(indol-3-yl)ethanols (TFIEs) is described by an enantioselective organocatalytic method from indoles and inexpensive trifluoroacetaldehyde methyl hemiacetal. The reaction is catalyzed by hydroquinine to produce TFIEs in an almost quantitative yield and w...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20982

    authors: Borkin DA,Landge SM,Török B

    更新日期:2011-09-01 00:00:00

  • Asymmetric allylation of α-ketoester-derived N-benzoylhydrazones promoted by chiral sulfoxides/N-oxides Lewis bases: highly enantioselective synthesis of quaternary α-substituted α-allyl-α-amino acids.

    abstract::Chiral sulfoxides/N-oxides (R)-1 and (R,R)-2 are effective chiral promoters in the enantioselective allylation of α-keto ester N-benzoylhydrazone derivatives 3a-g to generate the corresponding N-benzoylhydrazine derivatives 4a-g, with enantiomeric excesses as high as 98%. Representative hydrazine derivatives 4a-b were...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22159

    authors: Reyes-Rangel G,Bandala Y,García-Flores F,Juaristi E

    更新日期:2013-09-01 00:00:00

  • Enantioseparation of chiral perfluorooctane sulfonate (PFOS) by supercritical fluid chromatography (SFC): Effects of the chromatographic conditions and separation mechanism.

    abstract::Perfluorooctane sulfonate (PFOS) is one of the most frequently detected perfluoroalkyl substances in environmental and human samples. Previous studies have shown that nonracemic PFOS in biological samples can be used as a marker of PFOS exposure sources. In recent years, supercritical fluid chromatography (SFC) has em...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23120

    authors: Zhao L,Chen F,Guo F,Liu W,Liu K

    更新日期:2019-10-01 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

  • First molecules, biological chirality, origin(s) of life.

    abstract::Origin(s) of biological chirality appear(s) to be intimately connected to origin(s) of life. Prebiotic evolution toward these important turning points can be traced back to single chiral molecules. These can be small (monomeric) units as amino acids or monosaccharides or oligomers as oligo-RNA type molecules. Earlier ...

    journal_title:Chirality

    pub_type: 评论,杂志文章

    doi:10.1002/chir.20796

    authors: Caglioti L,Micskei K,Pályi G

    更新日期:2011-01-01 00:00:00

  • Organocatalytic aza-Michael/retro-aza-Michael reaction: pronounced chirality amplification in aza-Michael reaction and racemization via retro-aza-Michael reaction.

    abstract::A detailed experimental investigation of an aza-Michael reaction of aniline and chalcone is presented. A series of Cinchona alkaloid-derived organocatalysts with different functional groups were prepared and used in the aza-Michael and retro-aza-Michael reaction. There was an interesting finding that a complete revers...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20940

    authors: Cai YF,Li L,Luo MX,Yang KF,Lai GQ,Jiang JX,Xu LW

    更新日期:2011-05-01 00:00:00

  • HPLC enantioseparation and absolute configuration of novel anti-inflammatory pyrrole derivatives.

    abstract::The assignment of the absolute configuration of novel anti-inflammatory pyrrole derivatives has been accomplished by a combined strategy based on independent physical methods. The key step of our stereochemical characterization approach is the production at mg-scale of enantiomerically pure forms by HPLC on Chiralpak ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20518

    authors: Biava M,Cirilli R,Fares V,Ferretti R,Gallinella B,La Torre F,Poce G,Porretta GC,Supino S,Villani C

    更新日期:2008-06-01 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

  • 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

  • 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

  • Polymer-Supported Optically Active fac(S)-Tris(thiotato)rhodium(III) Complex for Sulfur-Bridging Reaction With Precious Metal Ions.

    abstract::The optically active mixed-ligand fac(S)-tris(thiolato)rhodium(III) complexes, ΔL -fac(S)-[Rh(aet)2 (L-cys-N,S)](-) (aet = 2-aminoethanethiolate, L-cys = L-cysteinate) () and ΔLL -fac(S)-[Rh(aet)(L-cys-N,S)2 ](2-) were newly prepared by the equatorial preference of the carboxyl group in the coordinated L-cys ligand. T...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22546

    authors: Aizawa S,Tsubosaka S

    更新日期:2016-01-01 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

  • Photo-ionization spectroscopy and mass spectrometry of some molecular and supramolecular asymmetric systems in the isolated state.

    abstract::Asymmetric molecular and supramolecular systems are characterized by: i. the circular dicroism in the angular distribution of valence photoelectrons emitted from randomly oriented chiral molecules by their interaction with circularly polarized VUV light; ii. the different stability and reactivity of diastereomeric agg...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20274

    authors: Giardini A,Paladini A,Catone D,Piccirillo S,Rondino F,Satta M,Filippi A,Speranza M,Turchini S,Zema N

    更新日期:2006-08-01 00:00:00

  • Comparative study on kynurenic acid production in the rat striatum by tryptophan enantiomers: an in vivo microdialysis study.

    abstract::Kynurenic acid (KYNA), an endogenous antagonist of N-methyl-D-aspartate and α(7) nicotinic acetylcholine receptors, is one of the L-tryptophan (Trp) metabolites. To compare the level of KYNA produced in the striatum of rats after independent administration of L-Trp and D-Trp, rats were intraperitoneally administered L...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20938

    authors: Ishii K,Iizuka H,Ogaya T,Song Z,Fukushima T

    更新日期:2011-01-01 00:00:00

  • Pharmacokinetics of nateglinide enantiomers and their metabolites in Goto-Kakizaki rats, a model for type 2 diabetes mellitus.

    abstract::The pharmacokinetics of (-)-N-(trans-4-isopropylcyclohexanecarbonyl)-D-phenylalanine (nateglinide) and its enantiomer (L-enantiomer) was studied in Goto-Kakizaki (GK) rats after intravenous administration of nateglinide or L-enantiomer at a dose of 40 micromol/kg body weight. Nateglinide, its L-enantiomer and their me...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20711

    authors: Tamura M,Shiba S,Kudo N,Kawashima Y

    更新日期:2010-01-01 00:00:00

  • Separation of Enantiomers of a Phospholipid in Langmuir Monolayers by a New Selector.

    abstract::Chiral discrimination in a racemic mixture of dipalmitoylphosphatidylcholine (DPPC) is induced by a new selector at the water-air interface: L-DPPC is segregated in the condensed phase of a Langmuir monolayer upon interactions with an enantiopure amphiphilic compound. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22508

    authors: Caminati G,Cicchi S,Lascialfari L,Brandi A

    更新日期:2015-11-01 00:00:00