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  Subjects -> CHEMISTRY (Total: 766 journals)
    - ANALYTICAL CHEMISTRY (45 journals)
    - CHEMISTRY (531 journals)
    - CRYSTALLOGRAPHY (22 journals)
    - ELECTROCHEMISTRY (24 journals)
    - INORGANIC CHEMISTRY (40 journals)
    - ORGANIC CHEMISTRY (40 journals)
    - PHYSICAL CHEMISTRY (64 journals)

CHEMISTRY (531 journals)                  1 2 3 4 5 6 | Last

2D Materials     Hybrid Journal  
Accreditation and Quality Assurance: Journal for Quality, Comparability and Reliability in Chemical Measurement     Hybrid Journal   (Followers: 31)
ACS Catalysis     Full-text available via subscription   (Followers: 23)
ACS Chemical Neuroscience     Full-text available via subscription   (Followers: 13)
ACS Combinatorial Science     Full-text available via subscription   (Followers: 7)
ACS Macro Letters     Full-text available via subscription   (Followers: 17)
ACS Medicinal Chemistry Letters     Full-text available via subscription   (Followers: 24)
ACS Nano     Full-text available via subscription   (Followers: 235)
ACS Photonics     Full-text available via subscription   (Followers: 2)
ACS Synthetic Biology     Full-text available via subscription   (Followers: 8)
Acta Chemica Iasi     Open Access  
Acta Chimica Slovaca     Open Access   (Followers: 5)
Acta Chromatographica     Full-text available via subscription   (Followers: 9)
Acta Facultatis Medicae Naissensis     Open Access   (Followers: 1)
Acta Metallurgica Sinica (English Letters)     Hybrid Journal   (Followers: 2)
adhäsion KLEBEN & DICHTEN     Hybrid Journal   (Followers: 2)
Adhesion Adhesives & Sealants     Hybrid Journal   (Followers: 4)
Adsorption Science & Technology     Full-text available via subscription   (Followers: 8)
Advanced Functional Materials     Hybrid Journal   (Followers: 32)
Advances in Chemical Engineering and Science     Open Access   (Followers: 21)
Advances in Chemical Science     Open Access   (Followers: 8)
Advances in Colloid and Interface Science     Full-text available via subscription   (Followers: 13)
Advances in Drug Research     Full-text available via subscription   (Followers: 17)
Advances in Fluorine Science     Full-text available via subscription   (Followers: 7)
Advances in Fuel Cells     Full-text available via subscription   (Followers: 12)
Advances in Heterocyclic Chemistry     Full-text available via subscription   (Followers: 8)
Advances in Materials Physics and Chemistry     Open Access   (Followers: 12)
Advances in Nanoparticles     Open Access   (Followers: 11)
Advances in Organometallic Chemistry     Full-text available via subscription   (Followers: 8)
Advances in Polymer Science     Hybrid Journal   (Followers: 38)
Advances in Protein Chemistry     Full-text available via subscription   (Followers: 6)
Advances in Protein Chemistry and Structural Biology     Full-text available via subscription   (Followers: 10)
Advances in Quantum Chemistry     Full-text available via subscription   (Followers: 4)
African Journal of Chemical Education     Open Access   (Followers: 1)
African Journal of Pure and Applied Chemistry     Open Access   (Followers: 2)
Afrique Science : Revue Internationale des Sciences et Technologie     Open Access  
Agrokémia és Talajtan     Full-text available via subscription   (Followers: 2)
Alchemy     Open Access   (Followers: 2)
Alkaloids: Chemical and Biological Perspectives     Full-text available via subscription   (Followers: 4)
AMB Express     Open Access   (Followers: 1)
American Journal of Applied Sciences     Open Access   (Followers: 27)
American Journal of Biochemistry and Biotechnology     Open Access   (Followers: 141)
American Journal of Biochemistry and Molecular Biology     Open Access   (Followers: 11)
American Journal of Chemistry     Open Access   (Followers: 17)
American Journal of Plant Physiology     Open Access   (Followers: 9)
American Mineralogist     Full-text available via subscription   (Followers: 2)
Analyst     Full-text available via subscription   (Followers: 34)
Angewandte Chemie     Hybrid Journal   (Followers: 14)
Angewandte Chemie International Edition     Hybrid Journal   (Followers: 188)
Annales UMCS, Chemia     Open Access   (Followers: 2)
Annual Reports in Computational Chemistry     Full-text available via subscription   (Followers: 1)
Annual Reports Section A (Inorganic Chemistry)     Full-text available via subscription   (Followers: 2)
Annual Reports Section B (Organic Chemistry)     Full-text available via subscription   (Followers: 4)
Annual Review of Chemical and Biomolecular Engineering     Full-text available via subscription   (Followers: 10)
Annual Review of Food Science and Technology     Full-text available via subscription   (Followers: 12)
Anti-Infective Agents     Hybrid Journal   (Followers: 1)
Applied Organometallic Chemistry     Hybrid Journal   (Followers: 4)
Applied Spectroscopy     Full-text available via subscription   (Followers: 12)
Applied Surface Science     Hybrid Journal   (Followers: 14)
Arabian Journal of Chemistry     Full-text available via subscription   (Followers: 6)
ARKIVOC     Open Access   (Followers: 1)
Asian Journal of Biochemistry     Open Access   (Followers: 1)
Australian Journal of Chemistry     Hybrid Journal   (Followers: 4)
Autophagy     Full-text available via subscription  
Avances en Quimica     Open Access   (Followers: 1)
Biochemical Pharmacology     Hybrid Journal   (Followers: 6)
Biochemistry     Full-text available via subscription   (Followers: 173)
Biochemistry Insights     Open Access   (Followers: 4)
Biochemistry Research International     Open Access   (Followers: 4)
BioChip Journal     Hybrid Journal   (Followers: 1)
Bioinorganic Chemistry and Applications     Open Access   (Followers: 4)
Biointerface Research in Applied Chemistry     Open Access   (Followers: 1)
Biointerphases     Open Access  
Biomacromolecules     Full-text available via subscription   (Followers: 17)
Biomass Conversion and Biorefinery     Partially Free   (Followers: 5)
Biomedical Chromatography     Hybrid Journal   (Followers: 7)
Biomolecular NMR Assignments     Hybrid Journal   (Followers: 2)
BioNanoScience     Partially Free   (Followers: 4)
Bioorganic & Medicinal Chemistry     Hybrid Journal   (Followers: 30)
Bioorganic & Medicinal Chemistry Letters     Hybrid Journal   (Followers: 24)
Bioorganic Chemistry     Hybrid Journal   (Followers: 5)
Biopolymers     Hybrid Journal   (Followers: 12)
Biosensors     Open Access   (Followers: 3)
Biotechnic and Histochemistry     Hybrid Journal   (Followers: 1)
Boletin de la Sociedad Chilena de Quimica     Open Access  
Bulletin of the Chemical Society of Ethiopia     Open Access   (Followers: 1)
Bulletin of the Chemical Society of Japan     Full-text available via subscription   (Followers: 12)
Canadian Association of Radiologists Journal     Full-text available via subscription   (Followers: 3)
Canadian Journal of Chemistry     Full-text available via subscription   (Followers: 6)
Canadian Mineralogist     Full-text available via subscription   (Followers: 1)
Carbohydrate Research     Hybrid Journal   (Followers: 10)
Carbon     Hybrid Journal   (Followers: 34)
Catalysis for Sustainable Energy     Open Access   (Followers: 1)
Catalysis Reviews: Science and Engineering     Hybrid Journal   (Followers: 4)
Catalysis Science and Technology     Free   (Followers: 4)
Catalysis Surveys from Asia     Hybrid Journal   (Followers: 4)
Catalysts     Open Access   (Followers: 6)
Cellulose     Hybrid Journal   (Followers: 4)
Central European Journal of Chemistry     Hybrid Journal   (Followers: 5)
Cereal Chemistry     Full-text available via subscription   (Followers: 3)

        1 2 3 4 5 6 | Last

Journal Cover Carbohydrate Research
   [12 followers]  Follow    
   Hybrid Journal Hybrid journal (It can contain Open Access articles)
     ISSN (Print) 0008-6215 - ISSN (Online) 0008-6215
     Published by Elsevier Homepage  [2563 journals]   [SJR: 0.675]   [H-I: 77]
  • Some Findings in Transgalactosylations Employing Modified Donor Substrates
    • Abstract: Publication date: Available online 18 August 2014
      Source:Carbohydrate Research
      Author(s): Lars Kröger , Joachim Thiem
      The scope of transgalactosylation with β-galactosidase (bovine testis) was studied employing a series of modified donor substrates based on p-nitrophenyl β-D-galactopyranoside and as uniform acceptor allyl 2-N-acetamido-2-deoxy-α-D-galactopyranoside. Structurally diverse donor molecules were recognized by the enzyme and led to novel disaccharide components, yet an excessive structural distortion was not accepted.
      Graphical abstract image

      PubDate: 2014-08-18T21:00:02Z
       
  • Facile nanofibrillation of chitin derivatives by gas bubbling and
           ultrasonic treatments in water
    • Abstract: Publication date: Available online 18 August 2014
      Source:Carbohydrate Research
      Author(s): Kohei Tanaka , Kazuya Yamamoto , Jun-ichi Kadokawa
      In this paper, we report that nanofiber network structures were constructed from chitin derivatives by gas bubbling and ultrasonic treatments in water. When chitin was first subjected to N2 gas bubbling with ultrasonication in water, the SEM images of the product showed nanofiber network morphology. However, nanofiber network was not re-constructed by the same N2 gas bubbling and ultrasonic treatments after agglomeration. We then have paid attention to an amidine group to provide the agglomeration-nanofibrillation behavior of chitin derivatives. An amidinated chitin was synthesized by the reaction of the amino groups in a partially deacetylated chitin with N,N-dimethylacetamide dimethyl acetal, which was subjected to CO2 gas bubbling and ultrasonic treatments in water to convert into an amidinium chitin by protonation. The SEM images of the product clearly showed nanofiber network morphology. We further examined re-nanofibrillation of the agglomerated material, which was obtained by mixing the nanofibrillated amidinium chitin with water, followed by drying under reduced pressure. Consequently, the material was re-nanofibrillated by N2 gas bubbling with ultrasonication in water owing to electrostatic repulsion between the amidinium groups. Furthermore, deprotonation of the amidinium chitin and re-protonation of the resulting amidinated chitin were conducted by alkaline treatment and CO2 gas bubbling-ultrasonic treatments, respectively. The material showed the agglomeration-nanofibrillation behavior during the processes.
      Graphical abstract image

      PubDate: 2014-08-18T21:00:02Z
       
  • Structural identification of 4-benzyl-voglibose hydrochloride monohydrate
           using NMR and single-crystal X-ray diffraction methods
    • Abstract: Publication date: Available online 12 August 2014
      Source:Carbohydrate Research
      Author(s): Fen-Fen Zhang , Yu-Qin Zhao , Jian-Ping Fan , Li-Gang Liu , Rui-Wen Li , Wen-Bin Shen , Ya Ding
      The chemical structure studies on an important related substance of voglibose have been carried out using NMR spectroscopy and single crystal X-ray crystallography. For the structure identification study, hydrochloride monohydrate of this compound was isolated and purified. Its molecular structure was characterized and analyzed using 1D (1H-NMR, 13C-NMR, and DEPT) and 2D (1H,1H-COSY, HSQC, HMBC, TOCSY, and ROESY) NMR spectra and the signal crystal structure was detected by X-ray crystallography. All results indicated this related substance of voglibose was C17H27NO7⋅HCl⋅H2O, 5,6-dideoxy-4-benzyl-5-{[2-hydroxy-1-(hydroxymethyl) ethy] amino }-1-C- (hydroxymethyl)-D-epi-inositol hydrochloride monohydrate.
      Graphical abstract image Highlights

      PubDate: 2014-08-14T20:53:24Z
       
  • Efficient synthesis of the tetrasaccharide repeating unit of the O-antigen
           of Escherichia coli O174 strain
    • Abstract: Publication date: Available online 12 August 2014
      Source:Carbohydrate Research
      Author(s): Ishani Bhaumik , Tamashree Ghosh , Anup Kumar Misra
      The tetrasaccharide repeating unit of the O-antigen of Escherichia coli O174 strain was synthesized applying sequential glycosylations of suitably functionalized monosaccharide intermediates. Activation of glycosyl trichloroacetimidate derivatives using nitrosyl tetrafluoroborate (NOBF4) has been used during the synthesis. The glycosylation steps were high yielding with satisfactory stereo outcome.
      Graphical abstract image Highlights

      PubDate: 2014-08-14T20:53:24Z
       
  • D-Glucose Derived Novel Gemini Surfactants: Synthesis and Study of Their
           Surface Properties, Interaction with DNA, and Cytotoxicity
    • Abstract: Publication date: Available online 14 August 2014
      Source:Carbohydrate Research
      Author(s): Vikash Kumar , Amrita Chatterjee , Nupur Kumar , Anasuya Ganguly , Indranil Chakraborty , Mainak Banerjee
      Four new D-glucose derived m-s-m type gemini surfactants with variable spacer and tail length have been synthesized by a simple and efficient synthetic methodology utilizing the free C-3 hydroxy group of diisopropylidene glucose. The synthetic route to these gemini surfactants with a quaternary ammonium group as polar head group involves a sequence of simple reactions including alkylation, imine formation, quaternization of amine etc. The surface properties of the new geminis were evaluated by surface tension and conductivity measurements. These gemini surfactants showed low cytotoxicity by MTT assay on HeLa cell line. The DNA binding capabilities of these surfactants were determined by agarose gel electrophoresis, fluorescence titration and DLS experiments. The preliminary studies by agarose gel electrophoresis indicated chain length dependent DNA binding abilities, further supported by ethidium bromide exclusion experiments. Two of the D-glucose derived gemini surfactants showed effective binding with pET-28a plasmid DNA (pDNA) at relatively low N/P ratio (i. e. cationic nitrogen/DNA phosphate molar ratio).
      Graphical abstract image Highlights

      PubDate: 2014-08-14T20:53:24Z
       
  • Structure and gene cluster of the O-antigen of Escherichia coli O68
    • Abstract: Publication date: Available online 12 August 2014
      Source:Carbohydrate Research
      Author(s): Lingyan Jiang , Andrei V. Perepelov , Andrei V. Filatov , Bin Liu , Alexander S. Shashkov , Sof’ya N. Senchenkova , Lei Wang , Yuriy A. Knirel
      The O-polysaccharide (O-antigen) of Escherichia coli O68 was studied by sugar analysis, partial solvolysis with anhydrous trifluoroacetic acid, and 1D and 2D 1H and 13C NMR spectroscopy. The following structure of the branched heptasaccharide repeating unit was established: The O-antigen gene cluster of E. coli O68 was sequenced. The gene functions were tentatively assigned by comparison with sequences in the available databases and found to be in full agreement with the O-antigen structure.
      Graphical abstract image

      PubDate: 2014-08-14T20:53:24Z
       
  • Synthesis, micellization and lectin binding of new glycosurfactants
    • Abstract: Publication date: Available online 5 August 2014
      Source:Carbohydrate Research
      Author(s): Alexandre G. Dal Bó , Valdir Soldi , Fernando C. Giacomelli , Christophe Travelet , Redouane Borsali , Sébastien Fort
      Here we report the preparation and physico-chemical characterization of carbohydrate-decorated micelles and their interaction with lectins. A library of biosourced amphiphiles was prepared by copper-catalyzed azide-alkyne cycloaddition (CuAAC) between alkynyl sugars (lactose, N-acetyl-D-glucosamine) and azido-functionalized poly(ethylene glycol) esters (N3- PEG900-decanoate (C10) and -dodecanoate (C12)). In water, these glycoconjugates self-assemble into micelles of homogeneous nanometric size (11 nm) as evidenced by scattering techniques (DLS for light, and SAXS for X-ray). A comparative study with previously synthesized octadecanoate counterparts pointed out that that nature of the fatty acid has no significant influence on the particle size but only affects their compactness. These findings are in favor of a possible bulk preparation from lipid mixtures such as those encountered in renewable vegetable oils. The presence of the carbohydrate epitopes on the surface of the micelles and their bioavailability for lectin targeting were also evidenced by light scattering measurements using wheat germ agglutinin (WGA) and peanut (Arachis Hypogaea) (PNA) lectins, supporting possible application as targeted drug nanocarriers.
      Graphical abstract image Highlights

      PubDate: 2014-08-10T20:44:14Z
       
  • Complex and mixture of β-cyclodextrin with diazepam characterised by
           1H NMR and atom-atom potential methods
    • Abstract: Publication date: Available online 7 August 2014
      Source:Carbohydrate Research
      Author(s): A. Pajzderska , J. Mielcarek , J. Wąsicki
      Inclusion complex of β-cyclodextrin with diazepam and a physical mixture of these components were studied by solid-state 1H NMR. The activation barrier for reorientation of the methyl group in the diazepam molecule was found not changed by complex formation with β-cyclodextrin. The complex formation resulted in a decrease in the number of water molecules and affected the relaxation time of β-cyclodextrin. By the atom-atom potential method the most probable configuration of the diazepam molecule inside β-cyclodextrin cavity was proposed.
      Graphical abstract image Highlights

      PubDate: 2014-08-10T20:44:14Z
       
  • Fluorous-based Carbohydrate Quartz Crystal Microbalance
    • Abstract: Publication date: Available online 7 August 2014
      Source:Carbohydrate Research
      Author(s): Lei Chen , Pengfei Sun , Guosong Chen
      Fluorous chemistry has brought many applications from catalysis to separation science, from supramolecular materials to analytical chemistry. However, fluorous-based Quartz Crystal Microbalance (QCM) has not been reported so far. In the current paper, fluorous interaction has been firstly utilized in QCM, and carbohydrate-protein interaction and carbohydrate-carbohydate interaction have been detected afterward.
      Graphical abstract image Highlights

      PubDate: 2014-08-10T20:44:14Z
       
  • Conformationally restricted
           3,5-O-(di-tert-butylsilylene)-d-galactofuranosyl thioglycoside donor for
           1,2-cis α-d-galactofuranosylation
    • Abstract: Publication date: Available online 7 August 2014
      Source:Carbohydrate Research
      Author(s): Mariano J. Tilve , Carola Gallo-Rodriguez
      A conformationally restricted 2-O-benzyl-3,5-O-di-tert-butylsilylene-β-D-thiogalactofuranoside donor was prepared from benzyl α-D-galactofuranoside and its donor capability was studied for stereoselective 1,2-cis α-d-galactofuranosylation. An unusual chemical behavior on benzylation and hydrogenolysis reactions was observed after the introduction of the 3,5-O-di-tert-butylsilylene protecting group into the galactofuranosyl moiety. The influence of the solvent, temperature and activating system was evaluated. The NIS/AgOTf system, widely used in 1,2-cis β-arabinofuranosylation, was not satisfactory enough for 1,2-cis galactofuranosylation. However, moderate to high α-selectivity was obtained with all the acceptors employed when used p-NO2PhSCl/AgOTf as a promoting system, in CH2Cl2 at -78 °C. The order of the addition of the reactants (premixing or preactivation) did not affect substantially the stereochemical course of the glycosylation reaction. The α-d-Galf-(1→6)-d-Man linkage was achieved with complete diastereoselectivity by preactivation of the conformationally constrained thioglycoside donor.
      Graphical abstract image Highlights

      PubDate: 2014-08-10T20:44:14Z
       
  • Advances in multifunctional glycosylated nanomaterials: preparation and
           applications in glycoscience
    • Abstract: Publication date: Available online 9 August 2014
      Source:Carbohydrate Research
      Author(s): Avijit K. Adak , Ben-Yuan Li , Chun-Cheng Lin
      The applications of glycosylated nanomaterials have gained considerable attention in recent years due to their unique structural properties and compatibility in biological systems. In this review, glyco-nanoparticles (glyco-NPs) are defined as compounds that contain a nano-sized metallic core, are composed of noble metals, magnetic elements, or binary inorganic nanoparticles, and that exhibit carbohydrate ligands on the surface in three dimensional polyvalent displays similar to the glycocalyx structures on cell membranes. Nanomaterials decorated with suitable biological recognition ligands have yielded novel hybrid nanobiomaterials with synergistic functions, especially in biomedical applications. This review focuses on strategies for building various types of glyco-NPs and highlights their potential in targeted drug delivery and molecular imaging as well as their uses in bioassays and biosensors. The most recent examples of glyco-NPs as vaccine candidates and probes for assaying enzymes with bond-forming activities are also discussed.
      Graphical abstract image Highlights

      PubDate: 2014-08-10T20:44:14Z
       
  • In(III) triflate-catalyzed detritylation and glycosylation by solvent-free
           ball milling
    • Abstract: Publication date: Available online 10 August 2014
      Source:Carbohydrate Research
      Author(s): Vajinder Kumar , Narender Yadav , K.P. Ravindranathan Kartha
      A highly efficient In(III) triflate-assisted method for the detritylation of O-trityl derivatives of carbohydrates, phenols and alcohols by solvent-free mechanochemical method is described. In the case of carbohydrates, further reaction in the presence of an acceptor sugar leads to highly efficient glycosylation in the same pot resulting in the formation of the desired glycoside-product in very high yields. The method was applied successfully to the synthesis of a combinatorial library of galactose-based (1,6)-linked cyclohexa-, hepta- and octasaccharides on gram scale.
      Graphical abstract image

      PubDate: 2014-08-10T20:44:14Z
       
  • Side reactions with 2,2,2-trichloroethoxysulfates during the synthesis of
           glycans
    • Abstract: Publication date: 19 September 2014
      Source:Carbohydrate Research, Volume 396
      Author(s): Kenya Matsushita , Yuta Sato , Shinji Funamoto , Jun-ichi Tamura
      Protected sulfate groups may be used as an alternative tool to provide sulfate esters at hydroxyl and amino groups, particularly on complex glycans. We examined 2,2,2-trichloroethoxysulfation at the mono-, di-, and trihydroxyl groups of saccharide moieties to show regioselective sulfation. We found some side reactions including inter- and intramolecular nucleophilic reactions with 2,2,2-trichloroethoxysulfates.
      Graphical abstract image

      PubDate: 2014-08-10T20:44:14Z
       
  • Heparin nanoparticles for β amyloid binding and mitigation of β
           amyloid associated cytotoxicity
    • Abstract: Publication date: Available online 2 August 2014
      Source:Carbohydrate Research
      Author(s): Peng Wang , Hovig Kouyoumdjian , David C. Zhu , Xuefei Huang
      Accumulation of β amyloid (Aβ) in the brain is believed to play a key role in the pathology of Alzheimer’s disease. Glycosaminoglycans on surface of neuronal cells can serve as nucleation sites to promote plaque formation on cell surface. To mimic this process, magnetic nanoparticles coated with heparin have been synthesized. The heparin nanoparticles were demonstrated to bind with Aβ through a variety of techniques including enzyme-linked immunosorbent assay, gel electrophoresis and thioflavin T assay. The nanoparticle exhibited little toxicity to neuronal cells and at the same time can effectively protect them from Aβ induced cytotoxicity. These results suggest that heparin nanoparticles can be a very useful tool for Aβ studies.
      Graphical abstract image

      PubDate: 2014-08-05T20:16:45Z
       
  • Preparation, characterisation and bioactivity evaluation of the inclusion
           complex formed between picoplatin and γ-cyclodextrin
    • Abstract: Publication date: Available online 1 August 2014
      Source:Carbohydrate Research
      Author(s): Jian-Qiang Zhang , Ke Li , Yan-Wei Cong , Shao-Ping Pu , Hong-You Zhu , Xiao-Guang Xie , Yi Jin , Jun Lin
      The inclusion complex of picoplatin with γ-cyclodextrin (γ-CD) was prepared and characterised by different analytical methods, including NMR, FTIR, TGA, phase solubility as well as SEM. All of these approaches indicated that picoplatin was able to form an inclusion complex with γ-CD, and that the picoplatin/γ-CD inclusion compounds exhibited different spectroscopic features and properties from free picoplatin. The stoichiometry of the complex was 1:1; the pyridine group of picoplatin was deeply inserted into the cavity of γ-CD and the amine platinum group of picoplatin was near the narrower rim of γ-CD. The calculated apparent stability constant of the complex was 10,318 M-1. Moreover, the water solubility of picoplatin was significantly improved, according to phase-solubility studies. The complex maintained its anticancer activity, as shown by an in vitro cell-survival assay on A549 and MCF-7 cancer cell lines. All of these results showed that inclusion complexation may be a promising strategy to design a novel formulation of picoplatin as an anticancer therapy.
      Graphical abstract image Highlights

      PubDate: 2014-08-01T20:01:10Z
       
  • Multivalent glycocyclopeptides: toward nano-sized glycostructures
    • Abstract: Publication date: Available online 1 August 2014
      Source:Carbohydrate Research
      Author(s): Gour Chand Daskhan , Nathalie Berthet , Baptiste Thomas , Michele Fiore , Olivier Renaudet
      Cyclopeptides have recently emerged as attractive molecular scaffolds for the multivalent presentation of carbohydrates in a well-defined constrained spatial orientation. This mini-review describes the last advances on the synthesis and the biological applications of these particular structures, going from low molecular weight glycoclusters to fully synthetic nano-sized glycodendrimers.
      Graphical abstract image Highlights

      PubDate: 2014-08-01T20:01:10Z
       
  • Assembling different antennas of the gp120 high mannose-type glycans on
           gold nanoparticles provides superior binding to the anti-HIV antibody 2G12
           than the individual antennas
    • Abstract: Publication date: Available online 30 July 2014
      Source:Carbohydrate Research
      Author(s): Fabrizio Chiodo , Pedro M. Enríquez-Navas , Jesús Angulo , Marco Marradi , Soledad Penadés
      In order to re-build Man9GlcNAc2 clusters of the HIV gp120 glycoprotein, ∼2 nm gold glyconanoparticles (GNPs) were coated with the synthetic partial structures of Man9, the tetramannoside Manα1-2Manα1-2Manα1-3Manα1- and the pentamannoside Manα1–2Manα1–3[Manα1–2Manα1–6]Manα1-. Their interactions with the anti-HIV broadly neutralizing antibody 2G12 were studied by Surface Plasmon Resonance (SPR)-based biosensors and saturation transfer difference (STD)-NMR spectroscopy. A synergistic effect of the tetra- and pentamannosides multimerised on a same GNP was observed. The assembly of these antennas of the gp120 high-mannose type glycan on GNPs provided superior binding to the anti-HIV antibody 2G12 respect to GNPs carrying only the individual oligomannosides. The results presented in this work provide new molecular information on the interactions between clusters of oligomannosides and 2G12 that could help in the design of a carbohydrate-based vaccine against HIV.
      Graphical abstract image Highlights

      PubDate: 2014-08-01T20:01:10Z
       
  • Montmorillonite K-10 promoted synthesis of chiral dioxa-caged compounds
           derived from levoglucosenone
    • Abstract: Publication date: Available online 1 August 2014
      Source:Carbohydrate Research
      Author(s): Mariano A. Zurita , Aylén Avila , Rolando A. Spanevello , Alejandra G. Suárez , Ariel M. Sarotti
      A short and efficient methodology for the synthesis of chiral dioxa-caged compounds from levoglucosenone, a biomass-derived enone, is herein presented. The key transformation, that involves a cascade 3-step cationic cyclization, was efficiently carried out in high yields and selectivities by Montmorillonite K-10 catalysis. The usefulness of K-10 in related semi-pinacol rearrangements to obtain pyran-3-ones is also shown. Interesting differences in the reactivity pattern was found for epimeric alcohols, and the origins of these findings were determined by DFT calculations.
      Graphical abstract image Highlights

      PubDate: 2014-08-01T20:01:10Z
       
  • Sweet graphene I: toward hydrophilic graphene nanosheets via click
           grafting alkyne-saccharides onto azide-functionalized graphene oxide
    • Abstract: Publication date: 19 September 2014
      Source:Carbohydrate Research, Volume 396
      Author(s): Mina Namvari , Hassan Namazi
      Water-soluble graphene nanosheets (GNS) were fabricated via functionalization of graphene oxide (GO) with mono and disaccharides on the basal plane and edges using Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition of azides and terminal alkynes (Click chemistry). To graft saccharides onto the plane of GO, it was reacted with sodium azide to introduce azide groups on the plane. Then, it was treated with alkyne-modified glucose, mannose, galactose, and maltose. In the next approach, we attached 1,3-diazideoprop-2-ol onto the edges of GO and it was subsequently clicked with alkyne-glucose. The products were analyzed by Fourier-transform infrared spectroscopy (FTIR), field-emission scanning electron microscopy, thermogravimetric analysis (TGA), and X-ray diffraction spectrometry. FTIR and TGA results showed both sugar-grafted GO sheets were reduced by sodium ascorbate during click-coupling reaction which is an advantage for this reaction. Besides, glycoside-grafted GNS were easily dispersed in water and stable for two weeks.
      Graphical abstract image

      PubDate: 2014-08-01T20:01:10Z
       
  • The use of O-trifluoroacetyl protection and profound influence of the
           nature of glycosyl acceptor in benzyl-free arabinofuranosylation
    • Abstract: Publication date: 19 September 2014
      Source:Carbohydrate Research, Volume 396
      Author(s): Polina I. Abronina , Ksenia G. Fedina , Nikita M. Podvalnyy , Alexander I. Zinin , Alexander O. Chizhov , Nikolay N. Kondakov , Vladimir I. Torgov , Leonid O. Kononov
      The influence of O-trifluoroacetyl (TFA) groups at different positions of thioglycoside glycosyl donors on stereoselectivity of α-arabinofuranosylation leading to corresponding disaccharides was studied. It was shown that TFA group in thioglycoside glycosyl donors, when combined with 2-O-(triisopropylsilyl) (TIPS) non-participating group, may be regarded as an electron-withdrawing protecting group that may enhance 1,2-cis-selectivity in arabinofuranosylation, the results strongly depending on the nature of glycosyl acceptor. The reactivities of the glycosyl donors were compared with those of a similar thioglycoside with O-pentafluoropropionyl groups and the known phenyl 3,5-O-(di-tert-butylsilylene)-1-thio-α-d-arabinofuranosides with 2-O-TIPS and 2-O-benzyl groups. The ‘matching’ in the donor–acceptor combination was found to be critical for achieving both high reactivity of glycosyl donor and β-stereoselectivity of arabinofuranosylation. The use of glycosyl donors with TFA and silyl protection may be useful in the realization of the benzyl-free approach to oligoarabinofuranosides with azido group in aglycon—convenient building blocks for the preparation of neoglycoconjugates.
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      PubDate: 2014-08-01T20:01:10Z
       
  • Editorial board
    • Abstract: Publication date: 18 August 2014
      Source:Carbohydrate Research, Volume 395




      PubDate: 2014-08-01T20:01:10Z
       
  • Graphical contents list
    • Abstract: Publication date: 18 August 2014
      Source:Carbohydrate Research, Volume 395




      PubDate: 2014-08-01T20:01:10Z
       
  • Stabilisation of ribofuranose by a mineral surface
    • Abstract: Publication date: Available online 1 August 2014
      Source:Carbohydrate Research
      Author(s): Thomas Georgelin , Maguy Jaber , Frédéric Fournier , Guillaume Laurent , France Costa-Torro , Marie-Christine Maurel , Jean-Francois Lambert
      The existence of the ribose moiety in biomolecules poses two problems for prebiotic chemistry. First, the exclusive presence of the furanose isomer in RNA has to be accounted for since furanose is a minor form in solution and does not exist in crystals. Second, all D-ribose polymorphs are unstable in aqueous medium so that a stabilisation mechanism has to be invoked. We observed that the adsorption on mineral surfaces as amorphous silica protects the sugar for degradation processes. Moreover, this silica surface, used as realistic chert model, is able to increase significantly the proportion of ribofuranose compared to ribopyranose forms. The interaction between surface and sugar was analysed by 13C NMR. Our results show a very significant chemical and thermal stabilisation of the adsorbed sugar by a silica surface and an almost twofold increase of ribofuranose compared to ribose in solution.
      Graphical abstract image

      PubDate: 2014-08-01T20:01:10Z
       
  • Does intramolecular hydrogen bond play a key role in the stereochemistry
           of α- and β-d-glucose?
    • Abstract: Publication date: 19 September 2014
      Source:Carbohydrate Research, Volume 396
      Author(s): Josué M. Silla , Rodrigo A. Cormanich , Roberto Rittner , Matheus P. Freitas
      Four α- and three β-isomers of the d-glucose were optimized in gas phase using ab initio (MP2) and DFT (ωB97X-D) methods, both using the aug-cc-pVDZ basis set. While earlier works suggest that the orientation of the hydroxyl groups is due to intramolecular hydrogen bonds (H-bonds), the present study reveals that most H-bonds forming five-membered rings are either weak or even do not exist. The quantum theory of atoms in molecules (QTAIM) analysis showed only a few cases of H-bond in d-glucose, particularly for those H-bonds forming six-membered rings, while the non-covalent interactions (NCI) analysis indicated that most intramolecular H-bonds are not strong enough to justify the counter-clockwise arrangement of the OH⋯O chains. Natural bond orbital analysis supported the findings obtained from QTAIM and NCI analyses and indicated that the anomeric effect for d-glucose in the gas phase is governed by a balance of steric, electrostatic, and hyperconjugative interactions.
      Graphical abstract image

      PubDate: 2014-08-01T20:01:10Z
       
  • The structure of O-polysaccharide isolated from Cronobacter universalis
           NCTC 9529T
    • Abstract: Publication date: Available online 29 July 2014
      Source:Carbohydrate Research
      Author(s): Kinga Marszewska , Małgorzata Czerwicka , Stephen J. Forsythe , Ewelina Sałdak , Sylwia Szulta , Halina Dziadziuszko , Karolina Ossowska , Zbigniew Kaczyński
      The O-polysaccharide (OPS) was isolated from Cronobacter universalis NCTC 9529T, a new species in the genus Cronobacter, which was created by the reclassification of the species Enterobacter sakazakii. Purified polysaccharide was analyzed by NMR spectroscopy (1H, COSY, TOCSY, ROESY, HSQC, and HSQC-TOCSY) and chemical methods. The monosaccharide derivatives were analyzed by gas chromatography, and gas chromatography-mass spectrometry. These experiments enabled the type and number of monosaccharides in the repeating unit of OPS, their positions of linkages, and absolute configuration to be determined. Together the chemical analysis established a structure of the OPS of C. universalis NCTC 9529T. OPS isolated from C. universalis was structurally characterized for the first time.
      Graphical abstract image Highlights

      PubDate: 2014-08-01T20:01:10Z
       
  • Polysaccharide-based nanocomposites and their applications
    • Abstract: Publication date: Available online 30 July 2014
      Source:Carbohydrate Research
      Author(s): Yingying Zheng , Jonathan Monty , Robert J. Linhardt
      Polysaccharide nanocomposites have become increasingly important materials over the past decade. Polysaccharides offer a green alternative to synthetic polymers in the preparation of soft nanomaterials. They have also been used in composites with hard nanomaterials, such as metal nanoparticles and carbon-based nanomaterials. This mini review describes methods for polysaccharide nanocomposite preparation and reviews the various types and diverse applications for these novel materials.
      Graphical abstract image Highlights

      PubDate: 2014-08-01T20:01:10Z
       
  • Quantitative fluorometric assay for the measurement of
           endo-1,4-β-glucanase
    • Abstract: Publication date: 18 August 2014
      Source:Carbohydrate Research, Volume 395
      Author(s): D. Mangan , B.V. McCleary , A. Liadova , R. Ivory , N. McCormack
      There is a growing demand for research tools to aid the scientific community in the search for improved cellulase enzymes for the biofuel industry. In this work, we describe a novel fluorometric assay for cellulase (endo-1,4-β-glucanase) which is based on the use of 4,6-O-benzylidene-4-methylumbelliferyl-β-cellotrioside (BzMUG3) in the presence of an ancillary β-glucosidase. This assay can be used quantitatively over a reasonable linear range, or qualitatively as a solution screening tool which may find extensive use in the area of metagenomics.
      Graphical abstract image

      PubDate: 2014-07-27T19:35:12Z
       
  • Functional identification of a galactosyltransferase critical to
           Bacteroides fragilis Capsular Polysaccharide A biosynthesis
    • Abstract: Publication date: 18 August 2014
      Source:Carbohydrate Research, Volume 395
      Author(s): Jerry M. Troutman , Sunita Sharma , Katelyn M. Erickson , Christina D. Martinez
      Capsular Polysaccharide A (CPSA), a polymer of a four-sugar repeating unit that coats the surface of the mammalian symbiont Bacteroides fragilis, has therapeutic potential in animal models of Multiple Sclerosis and other autoinflammatory diseases. Genetic studies have demonstrated that CPSA biosynthesis is dependent primarily on a single gene cluster within the B. fragilis genome. However, the precise functions of the individual glycosyltransferases encoded by this cluster have not been identified. In this report each of these glycosyltransferases (WcfQ, WcfP, and WcfN) have been expressed and tested for their function in vitro. Using a reverse phase high performance liquid chromatography (HPLC) assay, WcfQ and WcfP were found to transfer galactose from uridine diphosphate (UDP)-linked galactose (Gal) to N-acetyl-4-amino-6-deoxy-galactosamine (AADGal) linked to a fluorescent mimic of bactoprenyl diphosphate, the native isoprenoid anchor for bacterial polysaccharide biosynthesis. The incorporation of galactose to form a bactoprenyl-linked disaccharide was confirmed by radiolabel incorporation and mass spectrometry (MS) of purified product. Using varying concentrations of UDP-Gal and enzyme, WcfQ was found to be the most effective protein at transferring galactose, and is the most likely candidate for in vivo incorporation of the sugar. WcfQ also cooperated in the presence of three preceding biosynthetic enzymes to form an isoprenoid-linked disaccharide in a single-pot reaction. This work represents a critical step in understanding the biosynthetic pathway responsible for the formation of CPSA, an unusual and potentially therapeutic biopolymer.
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      PubDate: 2014-07-27T19:35:12Z
       
  • Synthesis and evaluation of α-, β-glucosidase inhibition of
           1-N-carboxamide-1-azafagomines and 5-epi-1-azafagomines
    • Abstract: Publication date: 18 August 2014
      Source:Carbohydrate Research, Volume 395
      Author(s): Raquel Mendes , Vera C.M. Duarte , António Gil Fortes , Maria J. Alves
      1-N-Carboxamide 1-azafagomines and 5-epi-1-azafagomines were obtained from 1-azafagomine and 5-epi-1-azafagomine. The hydroxyl groups and the N-2 pyridazine position were protected prior to reaction with different isocyanates to form ureas. Protective groups were removed leading to the target compounds in 18–23% global yields. Final compounds were tested towards α- and β-glucosidases.
      Graphical abstract image

      PubDate: 2014-07-27T19:35:12Z
       
  • Determination of native capsular polysaccharide structures of
           Streptococcus pneumoniae serotypes 39, 42, and 47F and comparison to
           genetically or serologically related strains
    • Abstract: Publication date: 18 August 2014
      Source:Carbohydrate Research, Volume 395
      Author(s): Bent O. Petersen , Sebastian Meier , Berit Smestad Paulsen , Antonio R. Redondo , Ian C. Skovsted
      The diversity of capsular polysaccharides of the bacterial pathogen Streptococcus pneumoniae leads to at least 91 different serotypes. While the genetic loci for capsular biosynthesis have been characterized for all serotypes, the determination of resultant polysaccharide structures remains incomplete. Here, we report the chemical structures of the capsular polysaccharides of serotypes 39, 42, and 47F from the genetic cluster 4, and discuss the structures in the context of structures from serologically and genetically related serotypes. Antigenic determinants can be approximated in this manner. The structure of the serotype 39 capsular polysaccharide is and has identical composition to the capsular polysaccharide 10A, but two different linkages. The serotype 42 structure closely resembles the genetically related serotype 35A, which does not contain residue A. The structure of the serotype 47F capsular polysaccharide is somewhat different from a recently determined structure from the same serogroup, while containing a structural motif that is reflected in serotype 35A and 42 capsular polysaccharide structures, thus explaining the cross-reactivity of serotype 47F with the typing serum 35a.
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      PubDate: 2014-07-27T19:35:12Z
       
  • A partially methylated mannogalactan from hybrid mushroom pfle 1p:
           purification, structural characterization, and study of immunoactivation
    • Abstract: Publication date: 18 August 2014
      Source:Carbohydrate Research, Volume 395
      Author(s): Prasenjit Maity , Manabendra Pattanayak , Saikat Maity , Ashis K. Nandi , Ipsita K. Sen , Birendra Behera , Tapas K. Maiti , Pijush Mallick , Samir R. Sikdar , Syed S. Islam
      A new water-soluble heteropolysaccharide (PS-II) with apparent molecular weight ∼1.65×105 Da, was isolated from the fruiting bodies of hybrid mushroom pfle 1p by hot aqueous extraction. It is composed of d-mannose, d-galactose, and 3-O-Me-d-galactose in a molar ratio of 1.0:0.99:1.1. The structural investigation of PS-II has been carried out using acid hydrolysis, methylation analysis, periodate oxidation study, and 1D/2D NMR experiments. Based on the results of these experiments, it was established that PS-II contained a main chain of (1→6) linked α-d-galactopyranosyl residues, one of which was substituted at C-2 by a terminal mannopyranosyl residue and also methylated at C-3 position. This heteropolysaccharide (PS-II) exhibited macrophage activation by NO production as well as in vitro splenocyte and thymocyte stimulation.
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      PubDate: 2014-07-27T19:35:12Z
       
  • Optical nonlinearity and electric conductivity origin study on sucrose
           crystal by using IR, Raman, INS, NMR, and EPR spectroscopies
    • Abstract: Publication date: 18 August 2014
      Source:Carbohydrate Research, Volume 395
      Author(s): M. Magdalena Szostak , Katarzyna Piela , Krystyna Hołderna-Natkaniec , Ireneusz Natkaniec , Ewa Bidzińska
      The supposed importance of hydrogen bonds toward the origin of second harmonic generation (SHG) and electric conductivity in crystalline sucrose was investigated by IR (4000–10cm−1), INS (2000–10cm−1, at 35K), polarized Raman (3600–50cm−1) spectra, and 1H NMR second moment line records in the temperature range 450–80K. The temperature dependence of NIR (7000–5500cm−1) polarized spectra gave information about –CH2 motions complementary to NMR results concerning –CH2OH group rearrangements. The EPR spectra were applied to study the generation of radical ions by exposure to NIR radiation. Density functional theory quantum chemical calculations were performed to reproduce the vibrational spectra in order to complete as far as possible the assignments of bands observed by us and in the literature in sucrose crystals, and to throw more light on the possible reasons of sucrose electric conductivity and optical nonlinearity by the knowledge of theoretical values of dipole moments, polarizabilities, first order hyperpolarizabilities of sucrose molecule and clusters as well as ionization energy and electron affinity. The proton transfer in one specific hydrogen bond parallel to the helical axis b is proposed to be the most important in SHG and conductivity origin.
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      PubDate: 2014-07-27T19:35:12Z
       
  • Simple synthesis of glycosylthiols and thioglycosides by rearrangement of
           O-glycosyl thionocarbamates
    • Abstract: Publication date: Available online 9 July 2014
      Source:Carbohydrate Research
      Author(s): A. Kasprzycka , R. Komor , G. Pastuch Gawołek , W. Szeja
      The synthesis of thioglycosides has been achieved in a high yielding process employing thionocarbamates prepared from protected reducing sugars and N-alkyl isothiocyanate in the presence of a non-nucleophilic base (K2CO3). In the key step of the synthesis, thionocarbamates were treated with Lewis acid (TMSOTf) to give O,S-rearrangement products that were applied to the synthesis of both anomers of heteroaryl thioglycosides.
      Graphical abstract image Highlights

      PubDate: 2014-07-27T19:35:12Z
       
  • Highly stereoselective synthesis of C-vinyl pyranosides via a Pd-mediated
           cycloetherification of 1-acetoxy-2,3-dideoxy-oct-2-enitols
    • Abstract: Publication date: Available online 16 July 2014
      Source:Carbohydrate Research
      Author(s): Ernest G. Nolen , Vivian C. Ezeh , Matthew J. Feeney
      Oct-2-enitols undergo a Pd°-mediated cyclization to produce C-vinyl α-gluco- and α-galactopyranosides, and C-vinyl β-mannopyranoside in good yield and with high stereoselectivity. While substrate control demonstrates a clear stereochemical preference during cyclization, the α- and β-epimeric ratios are enhanced by double diastereoselection using the (S,S) or (R,R)-DACH ligands.
      Graphical abstract image Highlights

      PubDate: 2014-07-27T19:35:12Z
       
  • Synthesis and Characterization of Copolyanhydrides of Carbohydrate-based
           Galactaric Acid and Adipic Acid
    • Abstract: Publication date: Available online 19 July 2014
      Source:Carbohydrate Research
      Author(s): Tuomas Mehtiö , Leena Nurmi , Virpi Rämö , Hannu Mikkonen , Ali Harlin
      A series of copolyanhydrides, consisting of 2,3,4,5-tetra-O-acetyl-galactaric acid (AGA) and adipic acid (AA) as monomer units, was polymerized. Synthesis of AGA monomer consisted of two steps. First, O-acetylation of galactaric acid secondary hydroxyl groups was performed using acetic anhydride as a reagent. Acetic anhydride was then further used as a reagent in the synthesis of diacetyl mixed anhydride of AGA. Polymerizations were conducted as bulk condensation polymerization at 150 °C. Thermal properties of the copolymers varied depending on monomer composition. Increase in the AGA content had a clear increasing effect on the Tg . Similar increasing effect was observed in Tm . The degree of crystallinity decreased as AGA content increased. There was a slightly lowering tendency in the molecular weights of the obtained polymers when the AGA content in the polymerization mixtures increased. The described synthesis route shows that bio-based aldaric acid monomers are potential candidates for the adjustment of thermal properties of polyanhydrides.
      Graphical abstract image Highlights

      PubDate: 2014-07-27T19:35:12Z
       
  • Structure and gene cluster organization of the O-antigen of Providencia
           alcalifaciens O45:H25
    • Abstract: Publication date: Available online 21 July 2014
      Source:Carbohydrate Research
      Author(s): Olga G. Ovchinnikova , Alexander S. Shashkov , Magdalena Moryl , Bin Liu , Antoni Rozalski , Yuriy A. Knirel
      O-polysaccharide was obtained by mild acid degradation of the lipopolysaccharide of Providencia alcalifaciens O45:H25 and studied by sugar analysis, Smith degradation, and 1H and 13C NMR spectroscopy. The following structure of the pentasaccharide repeat of the O-polysaccharide was established: The O-antigen gene cluster of P. alcalifaciens O45 was sequenced and found to be in full agreement with the O-polysaccharide structure established.
      Graphical abstract image Highlights

      PubDate: 2014-07-27T19:35:12Z
       
  • Identification of a new bis-amino acid glycoside selectively toxic to
           multiple myeloma cells
    • Abstract: Publication date: 23 July 2014
      Source:Carbohydrate Research, Volume 394
      Author(s): Chao-Ying Cheng , Yan-Yan Feng , Yi Zang , Jia Li , Xiao-Peng He , Guo-Rong Chen
      A bis-triazolyl phenylalaninyl galactoside was synthesized by a two-fold click reaction between an azido phenylalanine and a di-O-propynyl galactoside. By a cytotoxicity assay the compound was determined to be selectively toxic for multiple myeloma (MM) among a series of cancer cell lines with no toxicity to a control cell line. A Western blot analysis suggested that this compound could potentiate the cleavage of poly ADP-ribose polymerase in MM cells, leading to apoptosis.
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      PubDate: 2014-07-27T19:35:12Z
       
  • Useful approach to the synthesis of aryl thio- and selenoglycosides in the
           presence of rongalite
    • Abstract: Publication date: Available online 21 July 2014
      Source:Carbohydrate Research
      Author(s): Cheerladinne Venkateswarlu , Vibha Gautam , Srinivasan Chandrasekaran
      A simple, mild and cost effective methodology has been developed for the synthesis of aryl thio-and selenoglycosides from glycosyl halides and diaryl dichalcogenides. Diaryl dichalcogenides undergo reductive cleavage in the presence of rongalite (HOCH2SO2Na) to generate chalcogenate anion in situ followed by reaction with glycosyl halides to furnish the corresponding aryl thio- and selenoglycosides in excellent yields. Using this protocol, synthesis of 4-methyl-7-thioumbelliferyl-β-D-cellobioside (MUS-CB), a fluorescent non-hydrolyzable substrate analogue for cellulases has been achieved.
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      PubDate: 2014-07-27T19:35:12Z
       
  • Chemical synthesis of a tetrasaccharide related to the exocellular
           polysaccharide from Rhodococcus sp. RHA1
    • Abstract: Publication date: 23 July 2014
      Source:Carbohydrate Research, Volume 394
      Author(s): Darshita Budhadev , Balaram Mukhopadhyay
      Chemical synthesis of the tetrasaccharide related to the exocellular polysaccharide from Rhodococcus sp. RHA1 is reported. The stereoselective glycosylations were achieved by activation of the thioglycoside donors using N-iodosuccinimide in the presence of La(OTf)3 varying temperature per the need of 1,2-cis or 1,2-trans glycosylations. The target tetrasaccharide is reported in the form of its p-methoxyphenyl glycoside that can be cleaved selectively from the per-O-acetylated derivative allowing further glycoconjugate formation using trichloroacetimidate chemistry.
      Graphical abstract image

      PubDate: 2014-07-27T19:35:12Z
       
  • Editorial board
    • Abstract: Publication date: 23 July 2014
      Source:Carbohydrate Research, Volume 394




      PubDate: 2014-07-27T19:35:12Z
       
  • Graphical contents list
    • Abstract: Publication date: 23 July 2014
      Source:Carbohydrate Research, Volume 394




      PubDate: 2014-07-27T19:35:12Z
       
  • Revisiting synthetic preparation of the quorum sensing substrate
           S-d-ribosyl-l-homocysteine (SRH)
    • Abstract: Publication date: 23 July 2014
      Source:Carbohydrate Research, Volume 394
      Author(s): Megan E. Bolitho , Brendan J. Corcoran , Emily I. Showell-Rouse , Keeshia Q. Wang
      Cleavage of the thioether bond of S-d-ribosyl-l-homocysteine (SRH) by the enzyme S-ribosylhomocysteinase (LuxS) serves as the final biosynthetic step in the generation of the quorum sensing autoinducer AI-2 by bacteria. Herein, a revised chemical synthesis of SRH is presented at convenient scale and purity for in vitro studies of LuxS. Potassium bis(trimethylsilyl)amide (KHMDS) is identified as a judicious base for the formation of the thioether of the target compound from readily-accessible precursors: a thiol nucleophile derived from l-homocystine and a sulfonate-activated d-ribosyl electrophile. The exclusive use of acid-labile protecting groups allows for facile deprotection to the final product, producing the TFA salt of SRH in five synthetic steps and 26% overall yield. The chemically-synthesized material is isolated at high purity and demonstrated to serve as the LuxS substrate by an in vitro assay.
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      PubDate: 2014-07-27T19:35:12Z
       
  • A simplified procedure for gram-scale production of sialylglycopeptide
           (SGP) from egg yolks and subsequent semi-synthesis of Man3GlcNAc oxazoline
           
    • Abstract: Publication date: Available online 27 July 2014
      Source:Carbohydrate Research
      Author(s): Bingyang Sun , Wenzheng Bao , Xiaobo Tian , Mingjing Li , Hong Liu , Jinhua Dong , Wei Huang
      Heterogeneity of glycan structures in native glycoconjugates always hampers precise studies on carbohydrate-involved biological functions. To construct homogeneous glycoconjugates from natural resource of homogeneous glycans is therefore a practical approach to solve this problem. We report here an optimized procedure for gram-scale production of sialoglycopeptide (SGP) containing a disialyl biantennary complex-type N-glycan from egg yolks. Our new procedure simplified the extraction process by treating the egg yolk powder with 40% acetone, avoiding massive emulsification, high-speed centrifugation, and sophisticated chromatography in reported methods. Subsequent semi-synthesis of the N-glycan core Man3GlcNAc oxazoline from SGP was accomplished for the first-time via glyco-trimming and successive oxazoline formation. This efficient semi-synthesis provides an alternative to the pure chemical approach that involves multi-step total synthesis and facilitates the application of Endo-glycosidase-enabled chemoenzymatic synthesis of various homogeneous glycoconjugates.
      Graphical abstract image Highlights

      PubDate: 2014-07-27T19:35:12Z
       
  • Synthesis of octitols and the respective amino-derivatives from
           ‘organo-aldols’
    • Abstract: Publication date: Available online 27 July 2014
      Source:Carbohydrate Research
      Author(s): Katarzyna Łęczycka , Bartosz Chaciak , Maciej Cieplak , Piotr Cmoch , Sławomir Jarosz
      Two diastereoisomeric keto-octoses, obtained in there action of 2,3:4,5-diacetone-D-arabino se with protected dihydroxyacetone catalyzed with L- or D-proline, were converted into octitols by stereoselective reduction of the carbonyl group with zinc borohydride and final deprotection. The study on the preparation of the respective amino-derivatives by reductive amination of these organo-adducts is presented; stereochemical aspects of these processes are discussed.
      Graphical abstract image

      PubDate: 2014-07-27T19:35:12Z
       
  • Fucosylation of triethyleneglycol-based acceptors into
           “clickable” α-fucosides
    • Abstract: Publication date: Available online 14 June 2014
      Source:Carbohydrate Research
      Author(s): Shuai Wang , Nicolas Galanos , Audric Rousset , Kevin Buffet , Samy Cecioni , Dominique Lafont , Stéphane P. Vincent , Sébastien Vidal
      Design of multivalent glycoconjugates can find applications such as in anti-adhesive therapy against bacterial infections. Nevertheless, the access to such macromolecules requires functionalized building blocks prepared in a minimum number of steps and on a multi-gram scale at least for the laboratory. Fucose is a representative epitope used by several bacteria for adhesion to their host cells. The stereoselective, rapid and efficient access to two “clickable” α-fucosides was re-investigated using PPh3/CBr4-promoted glycosylation of chloro- (as precursors of azido-) and alkyne-functionalized triethyleneglycols with fully unprotected L-fucose. The convenient access to such building blocks paves the way to the design of new multivalent glycoconjugates functionalized with fucose epitopes and their applications.
      Graphical abstract image Highlights

      PubDate: 2014-06-14T15:16:04Z
       
  • Gadolinium-1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid
           conjugate of arabinogalactan as a potential liver-targeting magnetic
           resonance imaging contrast agent
    • Abstract: Publication date: Available online 6 June 2014
      Source:Carbohydrate Research
      Author(s): Yan Xiao , Rong Xue , Tianyan You , Xiaojing Li , Fengkui Pei , Xuxia Wang , Hao Lei
      A novel biocompatible macromolecule (AG-CM-EDA-DOTA-Gd) was synthesized as a liver magnetic resonance imaging (MRI) contrast agent. AG-CM-EDA-DOTA-Gd consisted of a carboxymethyl-arabinogalactan unit conjugated with gadolinium-1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (Gd-DOTA) via ethylenediamine, and was specifically designed to bind to hepatocyte asialoglycoprotein in vivo, in an effort to develop a potential new tool for the diagnosis of liver diseases. The T1-relaxivity (8.78 mmol-1·L·s-1) of AG-CM-EDA-DOTA-Gd was 1.86 times than that of Gd-DOTA (4.76 mmol-1·L·s-1) in D2O at 9.4 T and 25 °C. MRI experiments showed significant enhancement in rat liver following the intravenous administration of AG-CM-EDA-DOTA-Gd (0.094 mmol Gd3+/kg body weight), which persisted for longer than Gd-DOTA (0.098 mmol Gd3+/kg body weight). The mean percentage enhancements in the liver parenchyma were 85.2±6.5% and 19.3±3.3% for AG-CM-EDA-DOTA-Gd and Gd-DOTA, respectively. The results of this study therefore indicate that AG-CM-EDA-DOTA-Gd could be used as a potential liver-targeting contrast agent for MRI.
      Graphical abstract image Highlights

      PubDate: 2014-06-14T15:16:04Z
       
  • Synthesis of the allelochemical alliarinoside present in garlic mustard
           (Alliaria petiolata), an invasive plant species in North America
    • Abstract: Publication date: 23 July 2014
      Source:Carbohydrate Research, Volume 394
      Author(s): Carl Erik Olsen , Birger Lindberg Møller , Mohammed Saddik Motawia
      The allelochemical alliarinoside present in garlic mustard (Alliaria petiolata), an invasive plant species in North America, was chemically synthesized using an efficient and practical synthetic strategy based on a simple reaction sequence. Commercially available 1,2,3,4,6-penta-O-acetyl-β-d-glucopyranose was converted into prop-2-enyl 2′,3′,4′,6′-tetra-O-acetyl-β-d-glucopyranoside and subjected to epoxidation. In a one-pot reaction, ring-opening of the epoxide using TMSCN under solvent free conditions followed by treatment of the formed trimethylsilyloxy nitrile with pyridine and phosphoryl chloride, afforded the acetylated β-unsaturated nitriles (Z)-4-(2′,3′,4′,6′-tetra-O-β-d-glucopyranosyloxy)but-2-enenitrile and its isomer (E)-4-(2′,3′,4′,6′-tetra-O-β-d-glucopyranosyloxy)but-2-enenitrile. Deacetylation of Z- and/or E-isomers afforded the target molecules alliarinoside and its isomer.
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      PubDate: 2014-06-14T15:16:04Z
       
  • The O-specific polysaccharide of the marine bacterium Rheinheimera
           pacifica KММ 1406T containing d- and
           l-2-acetamido-2-deoxy-galacturonic acids
    • Abstract: Publication date: 23 July 2014
      Source:Carbohydrate Research, Volume 394
      Author(s): Nadezhda A. Komandrova , Maxim S. Kokoulin , Anatoliy I. Kalinovsky , Svetlana V. Tomshich , Lyudmila A. Romanenko , Victor E. Vaskovsky
      The O-specific polysaccharide was isolated from the lipopolysaccharide of Rheinheimera pacifica KММ 1406T and studied by chemical methods along with 1H and 13C NMR spectroscopy. It was shown that the polysaccharide contains one residue each of 2-acetamido-2-deoxy-d-galactose (d-GalNAc), 2-acetamido-2-deoxy-d- and 2-acetamido-2-deoxy-l-galacturonic acids (d-GalNAcA, l-GalNAcA), 2,4-diacetamido-2,4,6-trideoxy-d-glucose (d-QuiNAc4NAc), and 4-(N-acetyl-d-alanyl)amino-4,6-dideoxy-d-glucose (d-Qui4NAlaAc) and has the following structure: →4)-α-d-GalpNAc-(1→4)-α-l-GalpNAcA-(1→3)-β-d-QuipNAc4NAc-(1→2)-β-d-Quip4NDAlaAc-(1→4)-α-d-GalpNAcA-(1→
      Graphical abstract image

      PubDate: 2014-06-14T15:16:04Z
       
  • New ureas containing glycosyl and diphenylphosphinyl scaffolds: synthesis
           and the first attempts to use them in asymmetric synthesis
    • Abstract: Publication date: 23 July 2014
      Source:Carbohydrate Research, Volume 394
      Author(s): Stanisław Porwański
      Chiral ureas containing glycosyl and diphenylphosphinyl scaffolds were found to be an effective organocatalyst. They were synthesised in high yields by a one-pot tandem Staudinger/aza-Wittig coupling reaction. The first attempts of using them in asymmetric synthesis are presented. Yields of the Morita–Baylis–Hillman reaction were moderate with an enantiomeric excess of up to 80%.
      Graphical abstract image

      PubDate: 2014-06-14T15:16:04Z
       
  • Synthesis of hyaluronic acid oligosaccharides and exploration of a
           fluorous-assisted approach
    • Abstract: Publication date: 23 July 2014
      Source:Carbohydrate Research, Volume 394
      Author(s): Giuseppe Macchione , José L. de Paz , Pedro M. Nieto
      The synthesis of hyaluronic acid oligomers (tri- and tetrasaccharide) is described. We have followed a pre-glycosylation oxidation strategy. Glucuronic acid units were directly employed in coupling reactions with suitably protected glucosamine derivatives. In order to simplify the purification of synthetic intermediates, a fluorous-assisted strategy has been also explored. Using this approach, a hyaluronic acid trisaccharide was prepared.
      Graphical abstract image

      PubDate: 2014-06-14T15:16:04Z
       
 
 
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