Trisaccharides

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I Martinezcastro - One of the best experts on this subject based on the ideXlab platform.

Isabel Martínez-castro - One of the best experts on this subject based on the ideXlab platform.

Sándor Antus - One of the best experts on this subject based on the ideXlab platform.

  • Synthesis of the non-reducing end trisaccharide of the antithrombin-binding domain of heparin and its bioisosteric sulfonic acid analogues
    Tetrahedron, 2012
    Co-Authors: László Lázár, Mihály Herczeg, András Lipták, Sándor Antus, Erika Mező, Anikó Borbás
    Abstract:

    A glucoronic acid-containing trisaccharide related to the antithrombin-binding DEFGH domain of heparin and its methanesulfonic acid analogues were synthesized. Trisaccharides without sulfonic acid content or possessing a sulfonatomethyl moiety at position 2 or 6 of unit F were prepared in high yields by [DE+F] couplings using the same disaccharide uronate donor, respectively. Synthesis of the trisaccharide with a 3-deoxy-3-sulfonatomethyl function was accomplished in three different pathways, from which a [D+EF] coupling and applying a non-oxidized precursor of the glucuronic acid afforded the trisaccharide in the highest yield.

  • Synthesis of sulfonic acid analogues of the non-reducing end trisaccharide of the antithrombin binding domain of heparin
    Tetrahedron Letters, 2010
    Co-Authors: László Lázár, Mihály Herczeg, Anikó Fekete, Anikó Borbás, András Lipták, Sándor Antus
    Abstract:

    Three sulfonic acid Trisaccharides related to the antithrombin-binding DEFGH domain of heparin were synthesised. Trisaccharides carrying the sulfonatomethyl moiety at position 2 or 6 were prepared in high yields by [DE+F] couplings using the same disaccharide uronate donor and the appropriate sulfonic acid acceptor, respectively. The trisaccharide with a 3-deoxy-3-sulfonatomethyl function could be obtained with high efficacy by a [D+EF] coupling where the carboxylic function of the EF uronate acceptor was created at a disaccharide level.

  • Synthesis of three regioisomers of the pentasaccharide part of the Skp1 glycoprotein of Dictyostelium discoideum
    Tetrahedron-asymmetry, 2009
    Co-Authors: Zoltán Szabó, Mihály Herczeg, Anikó Fekete, Gyula Batta, Anikó Borbás, András Lipták, Sándor Antus
    Abstract:

    Abstract Three regioisomers of the linear pentasaccharide part of the Skp1 glycoprotein, found in Dictyostelium discoideum, were prepared in the form of (2-trimethylsilyl)ethyl glycosides by means of 2+3 block syntheses using the disaccharide donor at the non-reducing end, and three different trisaccharide acceptors at the reducing end. Fucosylation of (2-trimethylsilyl)ethyl 3,4,6-tri- O -benzyl-β- d -galactopyranosyl-(1→3)-4,6- O -benzylidene-2-deoxy-2- N Phth-β- d -glucopyranoside with different fucosyl donors carrying an O -(2-naphthyl)methyl ether as a temporary-protecting group at positions C2, C3 or C4 gave rise to the protected core Trisaccharides. After selective removal of the (2-naphthyl)methyl group, the resulting acceptors were glycosylated with the α(1→6) linked digalactosyl donor to yield the respective three regioisomeric pentasaccharides. Transformation of the phthalimido moiety into an N -acetyl group, followed by catalytic hydrogenation of the reducible-protecting groups furnished the free target pentasaccharides, which should be able to assist during the elucidation of the exact structure of the natural pentasaccharide.

Yuji Miyahara - One of the best experts on this subject based on the ideXlab platform.

  • Human influenza virus detection using sialyllactose-functionalized organic electrochemical transistors
    Sensors and Actuators B-chemical, 2018
    Co-Authors: Tatsuro Goda, Hiroaki Takeuchi, Shoji Yamaoka, Yukichi Horiguchi, Akira Matsumoto, Yuji Miyahara
    Abstract:

    Abstract An organic electrochemical transistor (OECT) with a trisaccharide-grafted conductive polymer channel was developed for human influenza A virus detection under aqueous conditions. A target recognition element was introduced into the electrochemical amplifier of the OECT for highly sensitive, selective, and label-free virus sensing. 3,4-Ethylenedioxythiophene (EDOT) and its derivative bearing an oxylamine moiety (EDOTOA) were electrochemically copolymerized on the channel region composed of a PEDOT:PSS thin film. The Trisaccharides composed of Sia-α2,6′-Gal-Glu (2,6-sialyllactose), a specific receptor for the hemagglutinin used as a spike protein on the surface of human influenza A virus, were covalently introduced into the EDOTOA unit. Changes in the drain current of the OECT were observed following virus adsorption onto the 2,6-sialyllactose-functionalized channel. A signal transduction mechanism involving a doping effect due to the adsorption of negatively-charged virus nanoparticles is proposed. The limit of detection was more than two orders of magnitude lower than commercial immunochromatographic influenza virus assays over the same detection time. Because of its processability with printing technologies and low power consumption, the OECT device developed here may be suitable for the wearable monitoring of influenza virus infection.

  • specific recognition of human influenza virus with pedot bearing sialic acid terminated Trisaccharides
    ACS Applied Materials & Interfaces, 2017
    Co-Authors: Wenfeng Hai, Tatsuro Goda, Hiroaki Takeuchi, Shoji Yamaoka, Yukichi Horiguchi, Akira Matsumoto, Yuji Miyahara
    Abstract:

    Conducting polymers are good candidates for biosensor applications when molecular recognition element is imparted. We developed trisaccharide-grafted conducting polymers for label-free detection of the human influenza A virus (H1N1) with high sensitivity and specificity. A 3,4-ethylenedioxythiophene (EDOT) derivative bearing an oxylamine moiety was electrochemically copolymerized with EDOT. The obtained film was characterized by cyclic voltammetry, X-ray photoelectron spectroscopy, scanning electron microscopy, stylus surface profilometer, and AC-impedance spectroscopy. The Trisaccharides comprising Sia-α2,6′-Gal-Glu (2,6-sialyllactose) or Sia-α2,3′-Gal-Glu (2,3-sialyllactose) were covalently introduced to the side chain of the conducting polymers as a ligand for viral recognition. Immobilization of sialyllactose was confirmed by quartz crystal microbalance (QCM) and water contact angle measurements. Specific interaction of 2,6-sialyllactose with hemagglutinin in the envelope of the human influenza A viru...

  • Specific Recognition of Human Influenza Virus with PEDOT Bearing Sialic Acid-Terminated Trisaccharides
    2017
    Co-Authors: Wenfeng Hai, Tatsuro Goda, Hiroaki Takeuchi, Shoji Yamaoka, Yukichi Horiguchi, Akira Matsumoto, Yuji Miyahara
    Abstract:

    Conducting polymers are good candidates for biosensor applications when molecular recognition element is imparted. We developed trisaccharide-grafted conducting polymers for label-free detection of the human influenza A virus (H1N1) with high sensitivity and specificity. A 3,4-ethylenedioxythiophene (EDOT) derivative bearing an oxylamine moiety was electrochemically copolymerized with EDOT. The obtained film was characterized by cyclic voltammetry, X-ray photoelectron spectroscopy, scanning electron microscopy, stylus surface profilometer, and AC-impedance spectroscopy. The Trisaccharides comprising Sia-α2,6′-Gal-Glu (2,6-sialyllactose) or Sia-α2,3′-Gal-Glu (2,3-sialyllactose) were covalently introduced to the side chain of the conducting polymers as a ligand for viral recognition. Immobilization of sialyllactose was confirmed by quartz crystal microbalance (QCM) and water contact angle measurements. Specific interaction of 2,6-sialyllactose with hemagglutinin in the envelope of the human influenza A virus (H1N1) was detected by QCM and potentiometry with enhanced sensitivity by 2 orders of magnitude when compared with that of commercially available kits. The developed conducting polymers possessing specific virus recognition are a good candidate material for wearable monitoring and point-of-care testing because of their processability and mass productivity in combination with printing technologies

Michal Brokl - One of the best experts on this subject based on the ideXlab platform.

  • characterization of o trimethylsilyl oximes of Trisaccharides by gas chromatography mass spectrometry
    Journal of Chromatography A, 2009
    Co-Authors: Michal Brokl, Ana C. Soria, María Luz Sanz, I Martinezcastro, Ana I Ruizmatute
    Abstract:

    Gas chromatography (GC) data (linear retention indices and relative areas) and mass spectra (most representative m/z fragments) of 12 reducing Trisaccharides as trimethylsilyl oximes (TMSO) and four non-reducing as trimethylsilyl (TMS) ethers have been described for the first time and related to their structural features. Some trends have been observed: earlier elution of non-reducing compounds and fructotrioses; aldotrioses bearing the reducing end with link in position 6 showing the highest retention. Abundance of several fragment ions and their ratios were useful for trisaccharide characterization; some of these features seem to be useful for the characterization of new Trisaccharides.

  • Characterization of O-trimethylsilyl oximes of Trisaccharides by gas chromatography–mass spectrometry
    Journal of chromatography. A, 2009
    Co-Authors: Michal Brokl, Ana C. Soria, Isabel Martínez-castro, María Luz Sanz, Ana I. Ruiz-matute
    Abstract:

    Gas chromatography (GC) data (linear retention indices and relative areas) and mass spectra (most representative m/z fragments) of 12 reducing Trisaccharides as trimethylsilyl oximes (TMSO) and four non-reducing as trimethylsilyl (TMS) ethers have been described for the first time and related to their structural features. Some trends have been observed: earlier elution of non-reducing compounds and fructotrioses; aldotrioses bearing the reducing end with link in position 6 showing the highest retention. Abundance of several fragment ions and their ratios were useful for trisaccharide characterization; some of these features seem to be useful for the characterization of new Trisaccharides.