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  Subjects -> CHEMISTRY (Total: 844 journals)
    - ANALYTICAL CHEMISTRY (47 journals)
    - CHEMISTRY (597 journals)
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CHEMISTRY (597 journals)                  1 2 3 | Last

Showing 1 - 200 of 735 Journals sorted alphabetically
2D Materials     Hybrid Journal   (Followers: 5)
Accreditation and Quality Assurance: Journal for Quality, Comparability and Reliability in Chemical Measurement     Hybrid Journal   (Followers: 25)
ACS Catalysis     Full-text available via subscription   (Followers: 25)
ACS Chemical Neuroscience     Full-text available via subscription   (Followers: 15)
ACS Combinatorial Science     Full-text available via subscription   (Followers: 23)
ACS Macro Letters     Full-text available via subscription   (Followers: 20)
ACS Medicinal Chemistry Letters     Full-text available via subscription   (Followers: 32)
ACS Nano     Full-text available via subscription   (Followers: 158)
ACS Photonics     Full-text available via subscription   (Followers: 6)
ACS Synthetic Biology     Full-text available via subscription   (Followers: 16)
Acta Chemica Iasi     Open Access  
Acta Chimica Sinica     Full-text available via subscription  
Acta Chimica Slovaca     Open Access   (Followers: 1)
Acta Chromatographica     Full-text available via subscription   (Followers: 8)
Acta Facultatis Medicae Naissensis     Open Access  
Acta Metallurgica Sinica (English Letters)     Hybrid Journal   (Followers: 4)
Acta Scientifica Naturalis     Open Access  
adhäsion KLEBEN & DICHTEN     Hybrid Journal   (Followers: 5)
Adhesion Adhesives & Sealants     Hybrid Journal   (Followers: 6)
Adsorption Science & Technology     Full-text available via subscription   (Followers: 4)
Advanced Functional Materials     Hybrid Journal   (Followers: 43)
Advanced Science Focus     Free   (Followers: 3)
Advances in Chemical Engineering and Science     Open Access   (Followers: 50)
Advances in Chemical Science     Open Access   (Followers: 11)
Advances in Chemistry     Open Access   (Followers: 9)
Advances in Colloid and Interface Science     Full-text available via subscription   (Followers: 14)
Advances in Drug Research     Full-text available via subscription   (Followers: 21)
Advances in Enzyme Research     Open Access   (Followers: 4)
Advances in Fluorine Science     Full-text available via subscription   (Followers: 8)
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: 15)
Advances in Nanoparticles     Open Access   (Followers: 12)
Advances in Organometallic Chemistry     Full-text available via subscription   (Followers: 13)
Advances in Polymer Science     Hybrid Journal   (Followers: 37)
Advances in Protein Chemistry     Full-text available via subscription   (Followers: 13)
Advances in Protein Chemistry and Structural Biology     Full-text available via subscription   (Followers: 13)
Advances in Quantum Chemistry     Full-text available via subscription   (Followers: 5)
Advances in Science and Technology     Full-text available via subscription   (Followers: 3)
African Journal of Bacteriology Research     Open Access  
African Journal of Chemical Education     Open Access   (Followers: 2)
African Journal of Pure and Applied Chemistry     Open Access   (Followers: 6)
Agrokémia és Talajtan     Full-text available via subscription   (Followers: 2)
Alkaloids: Chemical and Biological Perspectives     Full-text available via subscription   (Followers: 3)
AMB Express     Open Access   (Followers: 1)
Ambix     Hybrid Journal   (Followers: 3)
American Journal of Biochemistry and Biotechnology     Open Access   (Followers: 60)
American Journal of Biochemistry and Molecular Biology     Open Access   (Followers: 13)
American Journal of Chemistry     Open Access   (Followers: 23)
American Journal of Plant Physiology     Open Access   (Followers: 12)
American Mineralogist     Full-text available via subscription   (Followers: 8)
Anadolu University Journal of Science and Technology     Open Access  
Analyst     Full-text available via subscription   (Followers: 41)
Angewandte Chemie     Hybrid Journal   (Followers: 117)
Angewandte Chemie International Edition     Hybrid Journal   (Followers: 162)
Annales UMCS, Chemia     Open Access   (Followers: 1)
Annals of Clinical Chemistry and Laboratory Medicine     Open Access   (Followers: 1)
Annual Reports in Computational Chemistry     Full-text available via subscription   (Followers: 2)
Annual Reports Section A (Inorganic Chemistry)     Full-text available via subscription   (Followers: 3)
Annual Reports Section B (Organic Chemistry)     Full-text available via subscription   (Followers: 7)
Annual Review of Chemical and Biomolecular Engineering     Full-text available via subscription   (Followers: 9)
Annual Review of Food Science and Technology     Full-text available via subscription   (Followers: 13)
Anti-Infective Agents     Hybrid Journal   (Followers: 3)
Antiviral Chemistry and Chemotherapy     Full-text available via subscription  
Applied Organometallic Chemistry     Hybrid Journal   (Followers: 5)
Applied Spectroscopy     Full-text available via subscription   (Followers: 24)
Applied Surface Science     Hybrid Journal   (Followers: 22)
Arabian Journal of Chemistry     Open Access   (Followers: 6)
ARKIVOC     Open Access   (Followers: 2)
Asian Journal of Biochemistry     Open Access   (Followers: 1)
Atomization and Sprays     Full-text available via subscription   (Followers: 2)
Australian Journal of Chemistry     Hybrid Journal   (Followers: 4)
Autophagy     Hybrid Journal   (Followers: 2)
Avances en Quimica     Open Access   (Followers: 1)
Biochemical Pharmacology     Hybrid Journal   (Followers: 8)
Biochemistry     Full-text available via subscription   (Followers: 207)
Biochemistry Insights     Open Access   (Followers: 4)
Biochemistry Research International     Open Access   (Followers: 4)
BioChip Journal     Hybrid Journal  
Bioinorganic Chemistry and Applications     Open Access   (Followers: 8)
Bioinspired Materials     Open Access   (Followers: 2)
Biointerface Research in Applied Chemistry     Open Access   (Followers: 1)
Biointerphases     Open Access   (Followers: 1)
Biology, Medicine, & Natural Product Chemistry     Open Access  
Biomacromolecules     Full-text available via subscription   (Followers: 17)
Biomass Conversion and Biorefinery     Partially Free   (Followers: 11)
Biomedical Chromatography     Hybrid Journal   (Followers: 7)
Biomolecular NMR Assignments     Hybrid Journal   (Followers: 2)
BioNanoScience     Partially Free   (Followers: 4)
Bioorganic & Medicinal Chemistry     Hybrid Journal   (Followers: 91)
Bioorganic & Medicinal Chemistry Letters     Hybrid Journal   (Followers: 81)
Bioorganic Chemistry     Hybrid Journal   (Followers: 9)
Biopolymers     Hybrid Journal   (Followers: 17)
Biosensors     Open Access   (Followers: 1)
Biotechnic and Histochemistry     Hybrid Journal   (Followers: 2)
Bitácora Digital     Open Access  
Boletin de la Sociedad Chilena de Quimica     Open Access  
Bulletin of the Chemical Society of Ethiopia     Open Access   (Followers: 3)
Bulletin of the Chemical Society of Japan     Full-text available via subscription   (Followers: 25)
Bulletin of the Korean Chemical Society     Hybrid Journal  
C - Journal of Carbon Research     Open Access   (Followers: 2)
Canadian Association of Radiologists Journal     Full-text available via subscription   (Followers: 2)
Canadian Journal of Chemistry     Full-text available via subscription   (Followers: 6)
Canadian Mineralogist     Full-text available via subscription   (Followers: 3)
Carbohydrate Research     Hybrid Journal   (Followers: 27)
Carbon     Hybrid Journal   (Followers: 63)
Catalysis for Sustainable Energy     Open Access   (Followers: 5)
Catalysis Reviews: Science and Engineering     Hybrid Journal   (Followers: 7)
Catalysis Science and Technology     Free   (Followers: 5)
Catalysis Surveys from Asia     Hybrid Journal   (Followers: 3)
Catalysts     Open Access   (Followers: 6)
Cellulose     Hybrid Journal   (Followers: 4)
Cereal Chemistry     Full-text available via subscription   (Followers: 4)
ChemBioEng Reviews     Full-text available via subscription  
ChemCatChem     Hybrid Journal   (Followers: 6)
Chemical and Engineering News     Free   (Followers: 11)
Chemical Bulletin of Kazakh National University     Open Access  
Chemical Communications     Full-text available via subscription   (Followers: 63)
Chemical Engineering Research and Design     Hybrid Journal   (Followers: 20)
Chemical Research in Chinese Universities     Hybrid Journal   (Followers: 3)
Chemical Research in Toxicology     Full-text available via subscription   (Followers: 17)
Chemical Reviews     Full-text available via subscription   (Followers: 122)
Chemical Science     Open Access   (Followers: 18)
Chemical Technology     Open Access   (Followers: 11)
Chemical Vapor Deposition     Hybrid Journal   (Followers: 4)
Chemical Week     Full-text available via subscription   (Followers: 7)
Chemie in Unserer Zeit     Hybrid Journal   (Followers: 52)
Chemie-Ingenieur-Technik (Cit)     Hybrid Journal   (Followers: 25)
ChemInform     Hybrid Journal   (Followers: 4)
Chemistry & Biodiversity     Hybrid Journal   (Followers: 5)
Chemistry & Biology     Full-text available via subscription   (Followers: 29)
Chemistry & Industry     Hybrid Journal   (Followers: 2)
Chemistry - A European Journal     Hybrid Journal   (Followers: 110)
Chemistry - An Asian Journal     Hybrid Journal   (Followers: 12)
Chemistry and Materials Research     Open Access   (Followers: 15)
Chemistry Central Journal     Open Access   (Followers: 5)
Chemistry Education Research and Practice     Free   (Followers: 4)
Chemistry in Education     Open Access   (Followers: 2)
Chemistry International     Hybrid Journal   (Followers: 1)
Chemistry Letters     Full-text available via subscription   (Followers: 43)
Chemistry of Materials     Full-text available via subscription   (Followers: 138)
Chemistry of Natural Compounds     Hybrid Journal   (Followers: 8)
Chemistry-Didactics-Ecology-Metrology     Open Access  
ChemistryOpen     Open Access   (Followers: 1)
Chemkon - Chemie Konkret, Forum Fuer Unterricht Und Didaktik     Hybrid Journal  
Chemoecology     Hybrid Journal   (Followers: 2)
Chemometrics and Intelligent Laboratory Systems     Hybrid Journal   (Followers: 15)
Chemosensors     Open Access  
ChemPhysChem     Hybrid Journal   (Followers: 6)
ChemTexts     Hybrid Journal  
CHIMIA International Journal for Chemistry     Full-text available via subscription   (Followers: 3)
Chinese Journal of Chemistry     Hybrid Journal   (Followers: 6)
Chinese Journal of Polymer Science     Hybrid Journal   (Followers: 10)
Chromatographia     Hybrid Journal   (Followers: 24)
Chromatography     Open Access   (Followers: 5)
Chromatography Research International     Open Access   (Followers: 5)
Clay Minerals     Full-text available via subscription   (Followers: 9)
Cogent Chemistry     Open Access  
Colloid and Interface Science Communications     Open Access  
Colloid and Polymer Science     Hybrid Journal   (Followers: 8)
Colloids and Surfaces B: Biointerfaces     Hybrid Journal   (Followers: 6)
Combinatorial Chemistry & High Throughput Screening     Hybrid Journal   (Followers: 4)
Combustion Science and Technology     Hybrid Journal   (Followers: 18)
Comments on Inorganic Chemistry: A Journal of Critical Discussion of the Current Literature     Hybrid Journal   (Followers: 1)
Composite Interfaces     Hybrid Journal   (Followers: 3)
Comprehensive Chemical Kinetics     Full-text available via subscription   (Followers: 2)
Comptes Rendus Chimie     Full-text available via subscription  
Comptes Rendus Physique     Full-text available via subscription   (Followers: 1)
Computational and Theoretical Chemistry     Hybrid Journal   (Followers: 10)
Computational Biology and Chemistry     Hybrid Journal   (Followers: 9)
Computational Chemistry     Open Access   (Followers: 2)
Computers & Chemical Engineering     Hybrid Journal   (Followers: 9)
Coordination Chemistry Reviews     Full-text available via subscription  
Copernican Letters     Open Access  
Critical Reviews in Biochemistry and Molecular Biology     Hybrid Journal   (Followers: 4)
Crystal Structure Theory and Applications     Open Access   (Followers: 2)
CrystEngComm     Full-text available via subscription   (Followers: 7)
Current Catalysis     Hybrid Journal   (Followers: 1)
Current Metabolomics     Hybrid Journal   (Followers: 3)
Current Opinion in Colloid & Interface Science     Hybrid Journal   (Followers: 7)
Current Opinion in Molecular Therapeutics     Full-text available via subscription   (Followers: 14)
Current Research in Chemistry     Open Access   (Followers: 7)
Current Science     Open Access   (Followers: 28)
Dalton Transactions     Full-text available via subscription   (Followers: 17)
Detection     Open Access   (Followers: 2)
Developments in Geochemistry     Full-text available via subscription   (Followers: 1)
Diamond and Related Materials     Hybrid Journal   (Followers: 12)
Dislocations in Solids     Full-text available via subscription  
Doklady Chemistry     Hybrid Journal  
Drying Technology: An International Journal     Hybrid Journal   (Followers: 3)
Eclética Química     Open Access   (Followers: 1)
Ecological Chemistry and Engineering S     Open Access   (Followers: 2)
Ecotoxicology and Environmental Contamination     Open Access  
Educación Química     Open Access   (Followers: 1)
Education for Chemical Engineers     Hybrid Journal   (Followers: 4)
EDUSAINS     Open Access  
Elements     Full-text available via subscription   (Followers: 1)
Environmental Chemistry     Hybrid Journal   (Followers: 5)
Environmental Chemistry Letters     Hybrid Journal   (Followers: 2)
Environmental Science & Technology Letters     Full-text available via subscription   (Followers: 3)

        1 2 3 | Last

Journal Cover Carbohydrate Research
  [SJR: 0.654]   [H-I: 83]   [27 followers]  Follow
    
   Hybrid Journal Hybrid journal (It can contain Open Access articles)
   ISSN (Print) 0008-6215 - ISSN (Online) 0008-6215
   Published by Elsevier Homepage  [2969 journals]
  • Altered gene expression of glycosyltransferases and sialyltransferases and
           total amount of glycosphingolipids following herpes simplex virus
           infection
    • Abstract: Publication date: Available online 18 August 2016
      Source:Carbohydrate Research
      Author(s): Kazuki Miyaji, Jun-ichi Furukawa, Youichi Suzuki, Naoki Yamamoto, Yasuro Shinohara, Nobuhiro Yuki
      There is a case report of a patient with overlapping Guillain–Barré syndrome and Bickerstaff brainstem encephalitis after infection with herpes simplex virus type 1 (HSV-1), who carried high titers of serum anti-GQ1b IgG antibodies. Several studies have linked viral infection to the modulation of ganglioside expression such as human T-lymphotropic virus to GD2 and simian virus 40 to GM3. Also, enhancement of the expression of GM2 on the cell membrane after cytomegalovirus infection has been reported. The objective of this study was to unveil the relationship between HSV-1 infection and the alteration of cellular ganglioside expression in neuronal and glial cell lines. In addition to these cell lines, several human tumor cell lines including astrocytoma cells, neuroblastoma cells, T-cell leukemia cells and kidney cells derived from normal human and monkey were infected with HSV-1 as well as HSV-2. To measure changes in ganglioside-related gene expressions and gangliosides levels in cells, quantitative PCR and glycosphingolipid-glycomic analysis were performed. Changes in gene expression of glycosyltransferases and sialyltransferases were observed in HSV-1 and HSV-2-infected cells, although with different trends. 39 glycosphingolipid-glycans were quantitatively analyzed. HSV-1 and HSV-2 infections resulted in changes in the total amount of gangliosides depending on the cell lines used and type of virus. Qualitative changes caused by each infection of HSV-1 and HSV-2 were almost negligible.
      Graphical abstract image

      PubDate: 2016-08-20T00:28:39Z
       
  • Synthesis and glycosidase inhibition evaluation of
           (3S,4S)-3-((R)-1,2-dihydroxyethyl)pyrrolidine-3,4-diol
    • Abstract: Publication date: Available online 9 August 2016
      Source:Carbohydrate Research
      Author(s): En Zhang, Peng-Yan Bai, Wei Sun, Shang Wang, Ming-Ming Wang, Shuai-Min Xu, Hong-Min Liu
      A new azasugar (3S,4S)-3-((R)-1,2-dihydroxyethyl)pyrrolidine-3,4-diol (1) was obtained from commercially available d-glucose using one-pot reductive cyclization as a key step. The target product, i.e., the iminosugar isomer, was obtained in 10 steps and 24.3% overall yield. Only three column chromatography purifications were needed in this synthesis. The biological activity of the target molecule as glycosidase inhibitor was studied, but the inhibitory activity against four glycosidases was not good (IC50 > 100 μM).
      Graphical abstract image

      PubDate: 2016-08-12T15:03:35Z
       
  • Structure of repeating unit of the capsular polysaccharide from
           Acinetobacter baumannii D78 and assignment of the K4 gene cluster
    • Abstract: Publication date: 3 November 2016
      Source:Carbohydrate Research, Volume 434
      Author(s): Johanna J. Kenyon, Immacolata Speciale, Ruth M. Hall, Cristina De Castro
      The structure of the K4 capsular polysaccharide (CPS) from a multiply antibiotic resistant Acinetobacter baumannii isolate D78 was elucidated by chemical and spectroscopical analysis. The K4 repeating unit is composed entirely by aminosugars and the trisaccharide repeating unit of the backbone polysaccharide is branched with a terminal N-acetyl-galactosamine capped with pyruvate as cyclic acetal. Each residue is in the pyranose form, α configured at the anomeric center, and has the D absolute configuration. The genes responsible for the synthesis of the K4 repeat unit and its polymerization and export are found in the capsule locus KL4 present in D78. The pyruvate acetal addition to galactosamine is formed by Ptr1, a novel pyruvate transferase, encoded at this locus.
      Graphical abstract image

      PubDate: 2016-08-08T14:45:27Z
       
  • Structure of polysaccharide moiety of Pseudomonas xanthomarina KMM 1447T
           lipopolysaccharide
    • Abstract: Publication date: Available online 30 July 2016
      Source:Carbohydrate Research
      Author(s): Maxim S. Kokoulin, Svetlana V. Tomshich, Anatoly I. Kalinovskiy, Lyudmila A. Romanenko, Nadezhda A. Komandrova
      The structural analysis of a polysaccharide moiety of Pseudomonas xanthomarina KMM 1447T lipopolysaccharide (LPS) was carried out. Mild acid degradation of LPS resulted in identification of two polysaccharides. The major one was built of β-D-GlcpNAcA residues amidated with L-Ala and Gly residues randomly. The minor polysaccharide was composed of branched tetrasaccharide repeating units constituted by two D-Galр, D-GalpNAc and ether of D-Glc with (2R,4R)-2,4-dihydroxypentanoic acid lactone (2R,4R-Dhpl): →3)-α-D-Galр-(1 → 3)-β-D-Galр-(1 → 3)-[β-D-Glcp4(2R,4R-Dhpl)-(1 → 4)]-β-D-GalpNAc-(1 → .
      Graphical abstract image

      PubDate: 2016-08-04T14:30:44Z
       
  • Graphical contents list
    • Abstract: Publication date: 2 September 2016
      Source:Carbohydrate Research, Volume 432




      PubDate: 2016-08-04T14:30:44Z
       
  • New insights into Nod factor biosynthesis: Analyses of chitooligomers and
           lipo-chitooligomers of Rhizobium sp. IRBG74 mutants
    • Abstract: Publication date: Available online 3 August 2016
      Source:Carbohydrate Research
      Author(s): Véréna Poinsot, Matthew B. Crook, Stéphanie Erdn, Fabienne Maillet, Adeline Bascaules, Jean-Michel Ané
      Soil-dwelling, nitrogen-fixing rhizobia signal their presence to legume hosts by secreting lipo-chitooligomers (LCOs) that are decorated with a variety of chemical substituents. It has long been assumed, but never empirically shown, that the LCO backbone is synthesized first by NodC, NodB, and NodA, followed by addition of one or more substituents by other Nod proteins. By analyzing a collection of in-frame deletion mutants of key nod genes in the bacterium Rhizobium sp. IRBG74 by mass spectrometry, we were able to shed light on the possible substitution order of LCO decorations, and we discovered that the prevailing view is probably erroneous. We found that most substituents could be transferred to a short chitin backbone prior to acylation by NodA, which is probably one of the last steps in LCO biosynthesis. The existence of substituted, short chitin oligomers offers new insights into symbiotic plant–microbe signaling.
      Graphical abstract image

      PubDate: 2016-08-04T14:30:44Z
       
  • Editorial board
    • Abstract: Publication date: 2 September 2016
      Source:Carbohydrate Research, Volume 432




      PubDate: 2016-08-04T14:30:44Z
       
  • The O-antigen of Plesiomonas shigelloides serotype O36 containing
           pseudaminic acid
    • Abstract: Publication date: 3 November 2016
      Source:Carbohydrate Research, Volume 434
      Author(s): Marta Kaszowska, Katarina Stojkovic, Tomasz Niedziela, Czeslaw Lugowski
      The structure of the repeating unit of O-antigen of Plesiomonas shigelloides serotype O36 has been investigated by 1H and 13C NMR spectroscopy, matrix-assisted laser-desorption/ionization time-of-flight mass spectrometry and chemical methods. The new structure of trisaccharide has been established: →4)-β-Pse5Ac7(R3Hb)-(2 → 4)-β-D-Galp-(1 → 3)-β-D-GlcpNAc-(1→ These trisaccharide O-antigen units substitute the core undecasaccharide at C-4 of the β-D-GlcpNAc residue. The core oligosaccharide and lipid A are identical with these of the serotype O17 (PCM 2231) (Maciejewska, A., Lukasiewicz, J., Kaszowska, M., Jachymek, W., Man-Kupisinska, A.; Lugowski, C. Mar. Drugs. 2013, 11 (2), 440–454; Lukasiewicz, J., Dzieciatkowska, M., Niedziela, T., Jachymek, W., Augustyniuk, A., Kenne, L., Lugowski, C. Biochemistry, 2006, 45, 10434–10447).
      Graphical abstract image

      PubDate: 2016-08-04T14:30:44Z
       
  • The impact of aminopyrene trisulfonate (APTS) label in acceptor glycan
           substrates for profiling plant pectin β-galactosyltransferase
           activities
    • Abstract: Publication date: 4 October 2016
      Source:Carbohydrate Research, Volume 433
      Author(s): Stephan Goetz, Martin Rejzek, Sergey A. Nepogodiev, Robert A. Field
      Aminopyrene trisulfonate (APTS)-labelled disaccharides are demonstrated to serve as readily accessible acceptor substrates for galactosyltransferase activities present in Arabidopsis microsome preparations. The reductive amination procedure used to install the fluorophore results in loss of the ring structure of the reducing terminal sugar unit, such that a single intact sugar ring is present, attached via an alditol tether to the aminopyrene fluorophore. The configuration of the alditol portion of the labelled acceptor, as well as the position of alditol galactosylation, substantially influence the ability of compounds to serve as Arabidopsis galactosyltransferase acceptor substrates. The APTS label exhibits an unexpected reaction-promoting effect that is not evident for structurally similar sulfonated aromatic fluorophores ANDS and ANTS. When APTS-labelled β-(1 → 4)-Gal3 was employed as an acceptor substrate with Arabidopsis microsomes, glycan extension generated β-(1 → 4)-galactan chains running to beyond 60 galactose residues. These studies demonstrate the potential of even very short glycan-APTS probes for assessing plant galactosyltransferase activities and the suitability CE-LIF for CAZyme profiling.
      Graphical abstract image

      PubDate: 2016-08-04T14:30:44Z
       
  • Sequence analysis of the pyruvylated galactan sulfate-derived
           oligosaccharides by negative-ion electrospray tandem mass spectrometry
    • Abstract: Publication date: 4 October 2016
      Source:Carbohydrate Research, Volume 433
      Author(s): Na Li, Wenjun Mao, Xue Liu, Shuyao Wang, Zheng Xia, Sujian Cao, Lin Li, Qi Zhang, Shan Liu
      Five sulfated oligosaccharide fragments, F1–F5, were prepared from a pyruvylated galactan sulfate from the green alga Codium divaricatum, by partial depolymerization using mild acid hydrolysis and purification with gel-permeation chromatography. Negative-ion electrospray tandem mass spectrometry with collision-induced dissociation (ES-CID-MS/MS) is attempted for sequence determination of the sulfated oligosaccharides. The sequence of F1 with homogeneous disaccharide composition was first characterized to be Galp-(4SO4)-(1 → 3)-Galp by detailed nuclear magnetic resonance spectroscopic analyses. The fragmentation pattern of F1 in the product ion spectra was established on the basis of negative-ion ES-CID MS/MS, which was then applied to sequence analysis of other sulfated oligosaccharides. The sequences of F2 and F3 were deduced to be Galp-(4SO4)-(1 → 3)-Galp-(1 → 3)-Galp-(1 → 3)-Galp and 3,4-O-(1-carboxyethylidene)-Galp-(6SO4)-(1 → 3)-Galp, respectively. The sequences of major fragments in F4 and F5 were also deduced. The investigation demonstrated that negative-ion ES-CID-MS/MS was an efficient method for the sequence analysis of the pyruvylated galactan sulfate-derived oligosaccharides which revealed the patterns of substitution and glycosidic linkages. The pyruvylated galactan sulfate-derived oligosaccharides were novel sulfated oligosaccharides different from other algal polysaccharide-derived oligosaccharides.
      Graphical abstract image

      PubDate: 2016-07-29T14:07:10Z
       
  • 1,3-Dipolar cycloaddition of a cyclic nitrone derived from
           2-deoxy-D-ribose to α,β-unsaturated lactones: An entry to
           carbapenem antibiotics
    • Abstract: Publication date: 4 October 2016
      Source:Carbohydrate Research, Volume 433
      Author(s): Michał Pieczykolan, Olga Staszewska-Krajewska, Bartłomiej Furman, Marek Chmielewski
      1,3-Dipolar cycloadditions of 2-deoxy-D-ribose-derived L-threo five-membered cyclic nitrone to α,β-unsaturated γ- and δ-lactones were investigated. Cycloadducts obtained from δ-lactones, after N O bond cleavage, opening of the lactone ring, and protection of hydroxyl groups were subjected to β-lactam ring formation by using Mukaiyama's salt. Cycloadducts from γ-lactones subjected to the same reaction sequence undergo β-elimination of a water molecule to provide pyrrolidine-substituted unsaturated γ-lactones.
      Graphical abstract image

      PubDate: 2016-07-29T14:07:10Z
       
  • Stryphnosides G–P, 10 new triterpene glycosides from the pericarps
           of Stryphnodendron fissuratum
    • Abstract: Publication date: Available online 28 July 2016
      Source:Carbohydrate Research
      Author(s): Akihito Yokosuka, Genki Okabe, Satoru Tatsuno, Yoshihiro Mimaki
      Ten new triterpene glycosides, stryphnosides G–P (1–10), were isolated from the pericarps of Stryphnodendron fissuratum (Legminosae). The structures of 1–10 were determined based on spectroscopic analyses, including various two-dimensional NMR spectroscopic techniques, and the results of hydrolytic cleavage. The sugar moiety attached to C-3 of the aglycone of 4, 5, and 7–10 is composed of five or six monosaccharides, of which the terminal α-L-arabinosyl unit has a 1C4 conformation. Compounds 2 and 5 differ from the other isolates in having an α-L-rhamnosyl unit at the C-21 hydroxy group. The cytotoxic activity of 1–10, stryphnosides A–F (11–16), and their aglycones (1a, 11a, 14a, and 16a) against HL-60 cells was also examined.
      Graphical abstract image

      PubDate: 2016-07-29T14:07:10Z
       
  • Graphical contents list
    • Abstract: Publication date: 5 August 2016
      Source:Carbohydrate Research, Volume 431




      PubDate: 2016-07-25T13:58:46Z
       
  • Corrigendum to “Identification and structural determination of the
           capsular polysaccharides from two Acinetobacter baumannii clinical
           
    • Abstract: Publication date: 5 August 2016
      Source:Carbohydrate Research, Volume 431
      Author(s): Eleonora Fregolino, Valentina Gargiulo, Rosa Lanzetta, Michelangelo Parrilli, Otto Holst, Cristina De Castro



      PubDate: 2016-07-25T13:58:46Z
       
  • Editorial board
    • Abstract: Publication date: 5 August 2016
      Source:Carbohydrate Research, Volume 431




      PubDate: 2016-07-25T13:58:46Z
       
  • Discrimination of rat Brunner's gland carbohydrate antigens by
           site-specific monoclonal antibodies
    • Abstract: Publication date: 2 September 2016
      Source:Carbohydrate Research, Volume 432
      Author(s): Tomoyuki Chimuro, Hiroyuki Kuroyama, Yukinobu Goso, Kazuhiko Ishihara, Makoto Kurihara
      Mucus produced and secreted by gastrointestinal mucosa contains various types of mucins equipped with unique sugar chains considered to play critical roles in protecting mucous membranes; therefore, the identification and verification of mucin sugar chains is important for understanding the underlying mechanisms. In our previous work, we generated three monoclonal antibodies (mAbs), RGM22, RGM26, and RGM42, which recognize sugar chains in rat gastric mucin. Here, we immunohistochemically analyzed the rat gastrointestinal mucosa and found that the antigens recognized by RGM22 and RGM42 were expressed in the rat antrum and Brunner's glands, whereas that recognized by RGM26 was detected in the antrum, but rarely in Brunner's glands. We found that these antibodies reacted with porcine gastric mucin-derived oligosaccharides bearing a common structure: GalNAcα1-3(Fucα1-2)Galβ1-4GlcNAcβ1-6GalNAc-ol. Moreover, epitope analysis revealed that RGM42 and RGM22 recognized α-linked GalNAc and GalNAcα1-3Gal, respectively, on the GalNAcα1-3(Fucα1-2)Gal structure, whereas RGM26 was specific for GalNAcα1-3(Fucα1-2)Gal. These results indicate that rat Brunner's glands express specific antigens bearing GalNAcα1-3Gal that are recognized by RGM22 and RGM42. Thus, RGM22, RGM26, and RGM42 with their unique antigen specificities could be useful tools for investigation of oligosaccharide diversity among mucins.
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      PubDate: 2016-07-25T13:58:46Z
       
  • Conformational flexibility around the
           Gal-β-(1 → 3)-Glc linkage: Experimental evidence for
           the existence of the anti-ψ conformation in aqueous solution
    • Abstract: Publication date: 4 October 2016
      Source:Carbohydrate Research, Volume 433
      Author(s): Paloma Vidal, Jesús Jiménez-Barbero, Juan F. Espinosa
      NOE-based analysis of the disaccharide β-Gal-(1 → 3)-β-Glc-OMe (1), especially a diagnostic Gal1–Glc4 NOE detected in a HSQC-NOESY spectrum, reveals the existence of the anti-ψ conformer in aqueous solution in addition to the major syn conformer. This result provides experimental proof of conformational flexibility around the aglyconic bond of β-(1 → 3) disaccharides, in contrast to previous studies that suggested that the flexibility around this linkage was restricted to the syn conformational region.
      Graphical abstract image

      PubDate: 2016-07-25T13:58:46Z
       
  • Structure elucidation and gene cluster characterization of the O-antigen
           of Escherichia coli O80
    • Abstract: Publication date: Available online 14 July 2016
      Source:Carbohydrate Research
      Author(s): Sof'ya N. Senchenkova, Xi Guo, Andrei V. Filatov, Andrei V. Perepelov, Bin Liu, Alexander S. Shashkov, Yuriy A. Knirel
      Mild alkaline degradation of the lipopolysaccharide of Escherichia coli O80 afforded a polysaccharide, which was studied by sugar analysis, selective cleavage of glycosidic linkages, and 1H and 13C NMR spectroscopy. Solvolysis of the polysaccharide with CF3CO2H cleaved the linkages of α-Fuc and β-linked GlcNAc and GalNAc residues to give two disaccharides. The following structure of the hexasaccharide repeating unit of the O-polysaccharide was established: The polysaccharide repeat also contains a minor O-acetyl group but its position was not determined. The O-antigen gene cluster of E. coli O80 between the conserved galF and gnd genes was analyzed and found to be consistent with the O-polysaccharide structure established.
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      PubDate: 2016-07-17T13:25:18Z
       
  • Kinetic analysis for the isomerization of cellobiose to cellobiulose in
           subcritical aqueous ethanol
    • Abstract: Publication date: Available online 11 July 2016
      Source:Carbohydrate Research
      Author(s): Nontanut Soisangwan, Da-Ming Gao, Takashi Kobayashi, Pramote Khuwijitjaru, Shuji Adachi
      The isomerization of cellobiose to cellobiulose, and other degradation reactions of cellobiose were investigated in subcritical aqueous ethanol with concentrations of ethanol ranging from 0 to 60% (w/w) and at temperatures ranging from 170 to 200 °C. The maximum yield of cellobiulose (ca. 40%) was obtained from the treatment of cellobiose in 60% (w/w) aqueous ethanol at 190 °C. Glucose and fructose were also detected as byproducts. The concentration-time integral method was employed to analyze the rate constants for the isomerization and degradation processes. The rate constant of cellobiose isomerization to cellobiulose was greater than those of the degradation reactions under all experimental conditions, and it increased significantly with treatment temperature and ethanol concentration. However, the use of higher temperatures and ethanol concentrations was restricted due to decomposition of the saccharides and the low solubility of cellobiose, respectively. The effect of initial feed concentration (0.5–5.5% w/w) was also studied. The maximum productivity of cellobiulose, 54.1 kg/(h m3-reactor), was accomplished at a feed concentration of 5.5% (w/w) in 20% (w/w) subcritical aqueous ethanol.
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      PubDate: 2016-07-14T13:17:08Z
       
  • Efficient isomerization of methyl arabinofuranosides into corresponding
           arabinopyranosides in presence of pyridine
    • Abstract: Publication date: Available online 12 July 2016
      Source:Carbohydrate Research
      Author(s): Sunchu Prabhakar, Loïc Lemiègre, Thierry Benvegnu, Srinivas Hotha, Vincent Ferrières, Laurent Legentil
      Fisher glycosylation, the oldest but efficient reaction towards alkyl glycosides, suffers nonetheless from lack of selectivity, especially when dealing with pentoses. In this case, a mixture of the four isomers, namely the furanosides and the pyranosides, is formed. According to previous studies, the rate and selectivity of the reaction depend greatly on the reaction time and the temperature. In this report, another factor was evaluated, the introduction of a weak nucleophilic base. Interestingly, addition of pyridine few hours after the reaction has started allowed rapid isomerization of the methyl pentofuranosides into its pyranoside counterparts. The reaction proceeds with great diastereoselectivity using arabinose, ribose, xylose and lyxose as starting pentoses. Corresponding methyl pyranosides were obtained as the sole isomers with yields ranging from 65% to 75%.
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      PubDate: 2016-07-14T13:17:08Z
       
  • Human milk oligosaccharides: The role in the fine-tuning of innate immune
           responses
    • Abstract: Publication date: Available online 7 July 2016
      Source:Carbohydrate Research
      Author(s): Anna Kulinich, Li Liu
      In order to secure the health of newborns over the period of immune immaturity during the first months of life, a mother provides her offspring with passive protection: bioactive molecules transferred through the placenta and breast milk. It is well known that human milk contains immunoglobulins (Ig), immune cells and diverse cytokines, which affect newborn directly or indirectly and contribute to the maturation of immune system. However, in addition to the above-stated molecules, human milk oligosaccharides (HMOs), a complex mixture of free indigestible carbohydrates with multiple functions, play exceptional roles in the functioning of the infants' immune system. These biological molecules have been studied over decades, however, interest in HMOs does not seem to have abated. Although biological activities of oligosaccharides from human milk have been explicitly reviewed, information regarding the role of HMOs in inflammation remains rather fragmented. The purpose of this review is to compile existing knowledge about the role of certain species of HMOs, including fucosylated, galactosylated and sialylated oligosaccharides, and their signaling pathways in immunity and inflammation. The advances in applying this information to the treatment of diseases in infants as well as adults we also reviewed.
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      PubDate: 2016-07-10T13:09:16Z
       
  • Synthesis of C-glycosyl triazolyl quinoline-based fluorescent sensors for
           the detection of mercury ions
    • Abstract: Publication date: Available online 7 July 2016
      Source:Carbohydrate Research
      Author(s): Lingfang Wang, Jianzhong Jin, Linwei Zhao, Hongyun Shen, Chao Shen, Pengfei Zhang
      A series of novel C-glycosyl triazolyl quinoline-based fluorescent sensors have been synthesized via click chemistry. It was found that novel sensors exhibited good selectivity for Hg2+ over many other metal ions. The glucose framework was introduced to increase the water-solubility of the fluorescent sensors and broaden its application for the detection of Hg(II) in the water-solubility biological systems. The mechanism of the chemodosimetric behavior of the sensors has been attributed to a binding mode of triazolyl quinoline with Hg2+ which has been characterized by a number of spectroscopic techniques.
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      PubDate: 2016-07-10T13:09:16Z
       
  • Hyaluronic acid Auto-Crosslinked Polymer (ACP): Reaction Monitoring,
           Process Investigation and Hyaluronidase Stability
    • Abstract: Publication date: Available online 9 July 2016
      Source:Carbohydrate Research
      Author(s): Stefano Pluda, Mauro Pavan, Devis Galesso, Cristian Guarise
      Hyaluronic Acid (HA) is a non-sulphated glycosaminoglycan that, despite its high molecular weight, is soluble in water and is not resistant to enzymatic degradation, the latter of which hinders its wider application as a biomedical material. Auto-crosslinked polymer (ACP) gels of HA are fully biocompatible hydrogels that exhibit improved viscoelastic properties and prolonged in vivo residence times compared to the native polymer. Crosslinking is achieved through a base-catalysed reaction consisting of the activation of HA carboxyl groups by 2-chloro-1-methylpyridinium iodide (CMPI) and subsequent nucleophilic acyl substitution by the hydroxyl groups of HA in organic solvent. In this study, a number of ACP hydrogels have been obtained via reactions using varying ratios of CMPI to HA. The crosslinking reaction was monitored by rheological measurements in organic solvents during CMPI addition to the reaction mixture. The ACP intermediates, powders and hydrogels were characterized, helping to elucidate the crosslinking process. A two-step mechanism was proposed to explain the observed trends in viscosity and particle size. Syntheses were carried out by varying the reaction temperature, respectively at 0 °C, 25 °C and 45 °C in N-Methyl-2-Pyrrolidone (NMP), as well as the solvent respectively in NMP, DMSO and DMF at 25 °C. Interestingly, varying these parameters did not substantially affect the degree of crosslinking but likely did influence the intra/inter-molecular crosslinking ratio and, therefore, the viscoelastic properties. A wide range of crosslinking densities was confirmed through ESEM analysis. Finally, a comparative hyaluronidase degradation assay revealed that the ACPs exhibited a higher resistance toward enzymatic cleavage at low elastic modulus compared to other more chemically resistant, crosslinked HAs. These observations demonstrated the importance of crosslinking density of matrix structures on substrate availability.
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      PubDate: 2016-07-10T13:09:16Z
       
  • Multigram-scale synthesis of L,D-heptoside using a Fleming-Tamao oxidation
           promoted by mercuric trifluoroacetate
    • Abstract: Publication date: Available online 9 July 2016
      Source:Carbohydrate Research
      Author(s): Tianlei Li, Abdellatif Tikad, Maxime Durka, Weidong Pan, Stéphane P. Vincent
      An efficient multigram-scale synthesis of methyl 2,3,4,6-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside from methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside is reported. It involves a sequence of Swern oxidation, Grignard addition and Fleming-Tamao reactions. The resulting scaffold was used as a precursor to design a small library of clickable L-heptosides. This study shows that the use of mercuric bistrifluoroacetate is required both to accelerate and to cleanly perform the Fleming-Tamao oxidation, without side-reactions.
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      PubDate: 2016-07-10T13:09:16Z
       
  • Synthesis of a suite of click-compatible sugar analogs for probing
           carbohydrate metabolism
    • Abstract: Publication date: Available online 9 July 2016
      Source:Carbohydrate Research
      Author(s): Bo Wang, Daniel D. McClosky, Charles T. Anderson, Gong Chen
      Metabolic labeling based on the click chemistry between alkynyl and azido groups offers a powerful tool to study the function of carbohydrates in living systems, including plants. Herein, we describe the chemical synthesis of six alkynyl-modified sugars designed as analogs to D-glucose, D-mannose, L-rhamnose and sucrose present in plant cell walls. Among these new alkynyl probes, four of them are the 6-deoxy-alkynyl analogs of the corresponding sugars and do not possess any 6-OH groups. The other two are based on a new structural design, in which an ethynyl group is incorporated at the C-6 position of the sugar and the 6-OH group remains. The synthetic routes for both types of probes share common aldehyde intermediates, which are derived from the corresponding 6-OH precursor with other hydroxy groups protected. The overall synthesis sequence of these probes is efficient, concise, and scalable.
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      PubDate: 2016-07-10T13:09:16Z
       
  • Structural investigation of the lipopolysaccharide O-chain isolated from
           Burkholderia fungorum strain DSM 17061
    • Abstract: Publication date: Available online 9 July 2016
      Source:Carbohydrate Research
      Author(s): Antonia De Felice, Flaviana Di Lorenzo, Kirstin Scherlach, Claudia Ross, Alba Silipo, Christian Hertweck, Antonio Molinaro
      Gram-negative bacteria exhibit lipopolysaccharides (LPSs) on their outer membrane surface. LPS is considered one of the most potent bacterial virulence factors. Here we report the elucidation of the LPS O-chain structure isolated from Burkholderia fungorum, a bacterium isolated from the white-rot fungus Phanerochaete chrysosporium that can act as a pathogen for plants and domesticated animals. The structure was determined by the employment of detailed chemical and NMR spectroscopy analyses as the following:
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      PubDate: 2016-07-10T13:09:16Z
       
  • A novel analytical method for D-glucosamine quantification and its
           application in the analysis of chitosan degradation by a minimal enzyme
           cocktail
    • Abstract: Publication date: Available online 4 July 2016
      Source:Carbohydrate Research
      Author(s): Sophanit Mekasha, Hana Toupalová, Eka Linggadjaja, Harish A. Tolani, Ladislav Anděra, Magnus Ø. Arntzen, Gustav Vaaje-Kolstad, Vincent G.H. Eijsink, Jane W. Agger
      Enzymatic depolymerization of chitosan, a β-(1,4)-linked polycationic polysaccharide composed of D-glucosamine (GlcN) and N-acetyl-D-glucosamine (GlcNAc) provides a possible route to the exploitation of chitin-rich biomass. Complete conversion of chitosan to mono-sugars requires the synergistic action of endo- and exo- chitosanases. In the present study we have developed an efficient and cost-effective chitosan-degrading enzyme cocktail containing only two enzymes, an endo-attacking bacterial chitosanase, ScCsn46A, from Streptomyces coelicolor, and an exo-attacking glucosamine specific β-glucosaminidase, Tk-Glm, from the archaeon Thermococcus kodakarensis KOD1. Moreover, we developed a fast, reliable quantitative method for analysis of GlcN using high performance anion exchange chromatography with pulsed amperometric detection (HPAEC-PAD). The sensitivity of this method is high and less than 50 pmol was easily detected, which is about 1000-fold better than the sensitivity of more commonly used detection methods based on refractive index. We also obtained qualitative insight into product development during the enzymatic degradation reaction by means of ElectroSpray Ionization-Mass Spectrometry (ESI-MS).
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      PubDate: 2016-07-06T13:02:08Z
       
  • Novel biologically active series of N-acetylglucosamine derivatives for
           the suppressive activities on GAG release
    • Abstract: Publication date: Available online 5 July 2016
      Source:Carbohydrate Research
      Author(s): Tingting Cao, Yong Li, Lijuan Jiang, Li Yuan, Lin Dong, Ying Li, Shufan Yin
      (d)-Glucosamine and other nutritional supplements have emerged as safe alternative therapies for osteoarthritis, a chronic and degenerative articular joint disease. N-acetyl-(d)-glucosamine, a compound that can be modified at the N position, is considered to improve the oral bioavailability of (d)-glucosamine and has been proven to possess greater in vitro chondroprotective activity compared with the parent agent. In this study, to further utilize these properties, we focus on the modification of the N position with a benzenesulfonyl and different isoxazole formyl groups. Among these compounds, the 3-(2-chlorobenzene)-5-methyl-isoxazole formyl chloride and p-methoxybenzenesulfonyl chloride modifying structures proved to be the most active of the series and efficiently processed the chondrocytes in vitro. These novel N-position substitution compounds may represent promising leads for osteoarthritis drug development.
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      PubDate: 2016-07-06T13:02:08Z
       
  • Structure determination of Streptococcus suis serotype 9 capsular
           polysaccharide and assignment of functions of the cps locus genes involved
           in its biosynthesis
    • Abstract: Publication date: Available online 5 July 2016
      Source:Carbohydrate Research
      Author(s): Evgueny Vinogradov, Guillaume Goyette-Desjardins, Masatoshi Okura, Daisuke Takamatsu, Marcelo Gottschalk, Mariela Segura
      Streptococcus suis serotype 9 is the most prevalent S. suis serotype in several European countries. In spite of its pathogenicity for pigs and increasing zoonotic potential, limited information is available on this serotype. Here we determined for the first time the chemical composition and structure of serotype 9 capsular polysaccharide (CPS), a major bacterial virulence factor and the antigen at the origin of S. suis classification into serotypes. Chemical and spectroscopic data gave the repeating unit sequence: [3)Glcol-6-P-3-[D-Gal(α1-2)]D-Gal(β1-3)D-Sug(β1-3)L-Rha(α1-)] n . Compared to previously characterized S. suis CPS (serotypes 1, 1/2, 2 and 14), serotype 9 CPS does not contain sialic acid but contains a labile 4-keto sugar (2-acetamido-2,6-dideoxy-β-D-xylo-hexopyranos-4-ulose), one particular feature of this serotype. A correlation between S. suis serotype 9 CPS sequence and genes of this serotype cps locus encoding putative glycosyltransferases and polymerase responsible for the biosynthesis of the repeating unit was tentatively established. Knowledge of CPS structure and composition will contribute to better dissect the role of this bacterial component in the pathogenesis of S. suis serotype 9.
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      PubDate: 2016-07-06T13:02:08Z
       
  • Structural studies of a polysaccharide from Vibrio parahaemolyticus strain
           AN-16000
    • Abstract: Publication date: 2 September 2016
      Source:Carbohydrate Research, Volume 432
      Author(s): Carolina Fontana, Mona Zaccheus, Andrej Weintraub, Mohammad Ansaruzzaman, Göran Widmalm
      The structure of a polysaccharide from Vibrio parahaemolyticus strain AN-16000 has been investigated. The sugar and absolute configuration analysis revealed d-Glc, d-GalN, d-QuiN and l-FucN as major components. The PS was subjected to dephosphorylation with aqueous 40% HF to obtain an oligosaccharide that was analyzed by 1H and 13C NMR spectroscopy. The HR-MS spectrum of the oligosaccharide revealed a pentasaccharide composed of two Glc residues, one QuiNAc and one GalNAc, one FucNAc, as well as a glycerol moiety. The structure of the PS was determined using 1H, 13C, 15N and 31P NMR spectroscopy; inter-residue correlations were identified by 1H,13C-heteronuclear multiple-bond correlation, 1H,1H-NOESY and 1H,31P-hetero-TOCSY experiments. The PS backbone has the following teichoic acid-like structure: →3)-d-Gro-(1-P-6)-β-d-Glcp-(1→4)-α-l-FucpNAc-(1→3)-β-d-QuipNAc-(1→ with a side-chain consisting of α-d-Glcp-(1→6)-α-d-GalpNAc-(1→ linked to the O3 position of the FucNAc residue.
      Graphical abstract image

      PubDate: 2016-07-06T13:02:08Z
       
  • Synthesis of three different Galactose-based methacrylate monomers for the
           production of sugar-based polymers
    • Abstract: Publication date: Available online 28 June 2016
      Source:Carbohydrate Research
      Author(s): Jessica S. Desport, Daniele Mantione, Mónica Moreno, Haritz Sardón, María J. Barandiaran, David Mecerreyes
      Glycopolymers, synthetic sugar-containing macromolecules, are attracting ever-increasing interest from the chemistry community. Glycidyl methacrylate (GMA) is an important building block for the synthesis of sugar based methacrylate monomers and polymers. Normally, glycidyl methacrylate shows some advantages such as reactivity against nucleophiles or milder synthetic conditions such as other reactive methacrylate monomers. However, condensation reactions of glycidyl methacrylate with for instance protected galactose monomer leads to a mixture of two products due to a strong competition between the two possible pathways: epoxide ring opening or transesterification. In this paper, we propose two alternative routes to synthesize regiospecific galactose-based methacrylate monomers using the epoxy-ring opening reaction. In the first alternative route, the protected galactose is first oxidized to the acid in order to make it more reactive against the epoxide of GMA. In the second route, the GMA was first treated with epichlorohydrin followed by the epoxy ring opening reaction with methacrylic acid, to create an identical analogue of the ring-opening product of GMA. These two monomers were polymerized using conventional radical polymerization and were compared to the previously known galactose-methacrylate one. The new polymers show similar thermal stability but lower glass transition temperature (Tg) with respect to the known galactose methacrylate polymer.
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      PubDate: 2016-07-02T10:15:23Z
       
  • Application of amylomaltase for the synthesis of salicin-α-glucosides
           as efficient anticoagulant and anti-inflammatory agents
    • Abstract: Publication date: Available online 29 June 2016
      Source:Carbohydrate Research
      Author(s): Prakarn Rudeekulthamrong, Jarunee Kaulpiboon
      The focus of this study was the synthesis of α-glucosyl derivatives of salicin by a transglucosylation reaction. The reaction was catalyzed by recombinant amylomaltase using tapioca starch as a glucosyl donor. Several reaction parameters, such as the enzyme-substrate concentrations, pH, temperature and incubation time, were optimized. Using the optimum conditions, at least three products with retention times (R t) of 6.2, 9.2 and 14.1 were observed. The maximum yield of glucosylated salicin derivatives was 63% (w/w) of the total products. The structures of the glucosylated salicin derivatives were confirmed to be salicin-α-D-glucopyranoside, salicin-α-D-maltopyranoside and salicin-α-D-maltotriopyranoside through a combination of enzyme treatments, mass spectrometry and NMR analyses. The glycosidic bond between glucose units consisted of an α-1,4-configuration. The water solubility of salicin-α-D-glucopyranoside, salicin-α-D-maltopyranoside and salicin-α-D-maltotriopyranoside was 3-, 5- and 8-fold higher, respectively, than that of salicin, whereas their relative sweetness values were lower than that of sucrose. Interestingly, the long-chain salicin-α-D-glucosides showed greater anticoagulant and anti-inflammatory activities than salicin. In addition, the synthesized salicin-α-D-glucosides were able to tolerate acidic and high temperature conditions, but not α-glucosidase or human digestive enzymes. Therefore, these salicin-α-D-glucosides should be applied by the injection route to achieve greater bioavailability than is possible by the oral route.
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      PubDate: 2016-07-02T10:15:23Z
       
  • An integrated 3D-printed platform for the automated isolation of N-glycans
    • Abstract: Publication date: Available online 30 June 2016
      Source:Carbohydrate Research
      Author(s): Mao-Mao Wang, Pedro Laborda, Louis Patrick Conway, Xu-Chu Duan, Kun Huang, Li Liu, Josef Voglmeir
      The development of techniques for the rapid analysis of N-glycans is a key step in enabling the roles of glycoproteins in biological processes to be studied. Analysis is usually performed through the liberation of the carbohydrate moieties from proteins, followed by fluorescent labeling and identification using either standardized HPLC or mass spectrometry techniques. A simple and robust automated process for the release and isolation of N-glycans would greatly improve analytical throughput and reproducibility, and is thus highly desirable. Inspired by the increasing number of reported projects involving open source labware, which allows the design and construction of otherwise inaccessible laboratory equipment using low-cost 3D printers, we used this technique to fabricate a platform for the automated isolation of N-glycans. As a proof of concept, we demonstrated the successful recovery of glycan samples from the glycoprotein model fetuin using our self-made 3D-printed equipment.
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      PubDate: 2016-07-02T10:15:23Z
       
  • Synthesis of part structures of Cryptococcus neoformans serotype C
           capsular polysaccharide
    • Abstract: Publication date: Available online 1 July 2016
      Source:Carbohydrate Research
      Author(s): Lorenzo Guazzelli, Orla McCabe, Stefan Oscarson
      Cryptococcus neoformans is a fungal pathogen that can cause life-threatening infections in immunocompromised patients. The development of a vaccine based on the capsular polysaccharide of C. neoformans is still an open challenge due to the heterogeneity of the capsular polysaccharide and the difficulty of identifying protective epitopes. Therefore, construction of structurally defined part structures of the C. neoformans GXM capsule is in great demand. Herein is presented the synthesis of a 3-O-naphthalenylmethyl protected trisaccharide thioglycoside building block which is present in C. neoformans serotype C polysaccharide. Its property as a donor in a glycosylation reaction with a model acceptor has been evaluated together with its behaviour as an acceptor following removal of the temporary protecting group. The heavily branched hexasaccharide was obtained in good yields and excellent α-selectivity. The frame shifted octasaccharide structural triad motif for serotype C was also prepared following the same building block strategy. For the first time this structural motif, which is the most substituted amongst the four C. neoformans serotypes, was prepared. Three synthesized C. neoformans serotype C fragments of varying size, from penta-up to octasaccharide, were deprotected and will be included in unique glycoarrays to further investigate the possibility to develop a synthetic vaccine against this pathogen.
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      PubDate: 2016-07-02T10:15:23Z
       
  • Structure of the O-specific polysaccharides of Pseudomonas chlororaphis
           subsp. chlororaphis UCM B-106
    • Abstract: Publication date: Available online 1 July 2016
      Source:Carbohydrate Research
      Author(s): Evelina L. Zdorovenko, Alexandra A. Kadykova, Liudmyla D. Varbanets, Alexander S. Shashkov, Elena A. Kiprianova, Oksana S. Brovarskaya, Yuriy A. Knirel
      O-specific polysaccharide was obtained from the lipopolysaccharide of Pseudomonas chlororaphis subsp. chlororaphis UCM B-106 and studied by composition analysis along with 1D and 2D 1H and 13C NMR spectroscopy. The polysaccharide was found to contain a derivative of pseudaminic acid (Pse) and the following structure of the trisaccharide repeating unit was established. →4)-β-Psep5Ac7Hb-(2 → 6)-β-d-Galf-(1 → 3)-β-d-Galp-(1 → . Where Pse5Ac7Hb indicates 5-acetamido-3,5,7,9-tetradeoxy-7-[(R)-3-hydroxybutanoylamino]-l-glycero-l-manno-non-2-ulosonic acid.
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      PubDate: 2016-07-02T10:15:23Z
       
  • An unexpected rearrangement of pent-4-enofuranosides to cyclopentanones
           upon hydrogenolysis of the anomeric benzyl group
    • Abstract: Publication date: 2 September 2016
      Source:Carbohydrate Research, Volume 432
      Author(s): Shenyou Nie, Xiaoping Chen, Yuyong Ma, Wei Li, Biao Yu
      During our synthesis toward the unique nucleoside antibiotic A201A, we were surprised to find that a benzyl arabino-pent-4-enofuranoside underwent a Ferrier II-like rearrangement readily to provide the corresponding cyclopentanone derivative in high yield and stereoselectivity upon hydrogenolysis of the anomeric benzyl group.
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      PubDate: 2016-07-02T10:15:23Z
       
  • The first asymmetric synthesis of marliolide from readily accessible
           carbohydrate as chiral template
    • Abstract: Publication date: 2 September 2016
      Source:Carbohydrate Research, Volume 432
      Author(s): Karabasappa Mailar, Won Jun Choi
      A simple and efficient strategy for the first asymmetric total synthesis of marliolide was accomplished by using stereoselective alkylation of the dianion of the β-hydroxy lactone enolate with myristyl aldehyde as a key step. The key intermediate, β-hydroxyl γ-methyl butyrolactone was prepared by transformation of L-lyxonolactone starting from D-ribose, a naturally abundant chiral carbohydrate.
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      PubDate: 2016-06-27T15:11:49Z
       
  • Functional analysis of anomeric sugar kinases
    • Abstract: Publication date: 2 September 2016
      Source:Carbohydrate Research, Volume 432
      Author(s): Louis P. Conway, Josef Voglmeir
      Anomeric sugar kinases perform fundamental roles in the metabolism of carbohydrates. Under- or overexpression of these enzymes, or mutations causing functional impairments can give rise to diseases such as galactosaemia and so the study of this class of kinase is of critical importance. In addition, anomeric sugar kinases which are naturally promiscuous, or have been artificially made so, may find application in the synthesis of libraries of drug candidates (for example, antibiotics), and natural or unnatural oligosaccharides and glycoconjugates. In this review, we provide an overview of the biological functions of these enzymes, the tools which have been developed to investigate them, and the current frontiers in their study.
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      PubDate: 2016-06-27T15:11:49Z
       
  • Reduction of sugar lactones to hemiacetals with lithium
           triethylborohydride
    • Abstract: Publication date: 2 September 2016
      Source:Carbohydrate Research, Volume 432
      Author(s): Cesar Gonzalez, Sam Kavoosi, Andersson Sanchez, Stanislaw F. Wnuk
      Reduction of ribono-1,4-lactones and gulono-1,4-lactone as well as ribono-1,5-lactone and glucono-1,5-lactones with LTBH (1.2 equiv.) in CH2Cl2 at 0 °C for 30 min provided the corresponding pentose or hexose hemiacetals in high yields. Commonly used in carbohydrate chemistry protecting groups such as trityl, benzyl, silyl, acetals and to some extent acyls are compatible with this reduction.
      Graphical abstract image

      PubDate: 2016-06-23T14:53:40Z
       
  • A one-pot synthesis of 1,6,9,13-tetraoxadispiro(4.2.4.2)tetradecane by
           hydrodeoxygenation of xylose using a palladium catalyst
    • Abstract: Publication date: 2 September 2016
      Source:Carbohydrate Research, Volume 432
      Author(s): Michael A. Jackson, Judith A. Blackburn, Neil P.J. Price, Karl E. Vermillion, Steven C. Peterson, Gregory M. Ferrence
      In an effort to expand the number of biobased chemicals available from sugars, xylose has been converted to 1,6,9,13-tetraoxadispiro(4.2.4.2)tetradecane in a one-pot reaction using palladium supported on silica-alumina as the catalyst. The title compound is produced in 35–40% yield under 7 MPa H2 pressure at 733 K using 3–10 wt%Pd on silica-alumina catalyst. It is isolated using a combination of liquid-liquid extractions and flash chromatography. This dimer can be converted to its monomer, 2-hydroxy-(2-hydroxymethyl)tetrahydrofuran, which ring opens under acid conditions to 1,5-dihydroxy-2-pentanone. This diol can then be esterified with vinylacetate in phosphate buffer to produce 1,5-bis(acetyloxy)-2-pentanone which is an inhibitor of mammalian 11β-hydroxysteroid dehydrogenase 1. 1H and 13C nmr spectra of each of these species are reported. The single crystal X-ray structure of the title compound is also reported. These data were collected in a temperature range of 100 K–273 K and show a solid state phase change from triclinic to monoclinic between 175 K and 220 K without a conformational change.
      Graphical abstract image

      PubDate: 2016-06-23T14:53:40Z
       
  • Comprehensive analysis of the N-glycan biosynthetic pathway using
           bioinformatics to generate UniCorn: A theoretical N-glycan structure
           database
    • Abstract: Publication date: 5 August 2016
      Source:Carbohydrate Research, Volume 431
      Author(s): Yukie Akune, Chi-Hung Lin, Jodie L. Abrahams, Jingyu Zhang, Nicolle H. Packer, Kiyoko F. Aoki-Kinoshita, Matthew P. Campbell
      Glycan structures attached to proteins are comprised of diverse monosaccharide sequences and linkages that are produced from precursor nucleotide-sugars by a series of glycosyltransferases. Databases of these structures are an essential resource for the interpretation of analytical data and the development of bioinformatics tools. However, with no template to predict what structures are possible the human glycan structure databases are incomplete and rely heavily on the curation of published, experimentally determined, glycan structure data. In this work, a library of 45 human glycosyltransferases was used to generate a theoretical database of N-glycan structures comprised of 15 or less monosaccharide residues. Enzyme specificities were sourced from major online databases including Kyoto Encyclopedia of Genes and Genomes (KEGG) Glycan, Consortium for Functional Glycomics (CFG), Carbohydrate-Active enZymes (CAZy), GlycoGene DataBase (GGDB) and BRENDA. Based on the known activities, more than 1.1 million theoretical structures and 4.7 million synthetic reactions were generated and stored in our database called UniCorn. Furthermore, we analyzed the differences between the predicted glycan structures in UniCorn and those contained in UniCarbKB (www.unicarbkb.org), a database which stores experimentally described glycan structures reported in the literature, and demonstrate that UniCorn can be used to aid in the assignment of ambiguous structures whilst also serving as a discovery database.
      Graphical abstract image

      PubDate: 2016-06-18T12:40:13Z
       
  • A β-agarase with high pH stability from Flammeovirga sp. SJP92
    • Abstract: Publication date: 2 September 2016
      Source:Carbohydrate Research, Volume 432
      Author(s): Qi Dong, Lingwei Ruan, Hong Shi
      A novel endo-type β-agarase, AgaB, was cloned from an agar-degrading bacterium, Flammeovirga sp. SJP92. The gene agaB consists of 2, 550 bp and encodes a protein of 849 amino acids including a 19 amino acids signal peptide. Based on the amino acid sequence similarity, AgaB belongs to the glycoside hydrolase family GH16. The recombinant AgaB was expressed in Escherichia coli and exhibited maximal activity at around 45 °C and pH 8.0, with a specific activity of 254.2 U/mg, a K m of 3.99 mg/ml and a V max of 700 U/mg for agarose. The agarase was stable at neutral to mildly alkaline condition, and remained 85%–90% of activity after treatment for 1 h, a characteristic much more different from other agarases reported. The recombinant enzyme was sensitive to some metal ions (Cu2+, Co2+ and Zn2+), but resistant to some denaturants (urea and SDS). It can hydrolyze the β-1, 4-glycosidic linkages of agarose, yielding neoagarotetraose and neoagarohexaose as the main products. These properties could make AgaB has a potential application in the food, cosmetic and medical industries.
      Graphical abstract image

      PubDate: 2016-06-18T12:40:13Z
       
  • The comparison of glycosphingolipids isolated from an epithelial ovarian
           cancer cell line and a nontumorigenic epithelial ovarian cell line using
           MALDI-MS and MALDI-MS/MS
    • Abstract: Publication date: 5 August 2016
      Source:Carbohydrate Research, Volume 431
      Author(s): Krishani K. Rajanayake, William R. Taylor, Dragan Isailovic
      Glycosphingolipids (GSLs) are important biomolecules, which are linked to many diseases such as GSL storage disorders and cancer. Consequently, the expression of GSLs may be altered in ovarian cancer cell lines in comparison to apparently healthy cell lines. Here, differential expressions of GSLs in an epithelial ovarian cancer cell line SKOV3 and a nontumorigenic epithelial ovarian cell line T29 were studied using matrix-assisted laser desorption/ionization-mass spectrometry (MALDI-MS) and MALDI-MS/MS. The isolation of GSLs from SKOV3 and T29 cell lines was carried out using Folch partition. GSLs were successfully detected by MALDI-MS, and structurally assigned by a comparison of their MALDI-MS/MS fragmentation patterns with MS/MS data found in SimLipid database. Additionally, LIPID MAPS was used to assign GSL ion masses in MALDI-MS spectra. Seventeen neutral GSLs were identified in Folch partition lower (chloroform/methanol) phases originating from both cell lines, while five globo series neutral GSLs were identified only in the Folch partition lower phase of SKOV3 cell line. Several different sialylated GSLs were detected in Folch partition upper (water/methanol) phases of SKOV3 and T29 cell lines. Overall, this study demonstrates the alteration and increased glycosylation of GSLs in an epithelial ovarian cancer cell line in comparison to a nontumorigenic epithelial ovarian cell line.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Rapid synthesis of linear homologous oligoarabinofuranosides related to
           mycobacterial lipoarabinomannan and a neoglycoconjugate thereof
    • Abstract: Publication date: 5 August 2016
      Source:Carbohydrate Research, Volume 431
      Author(s): Nikita M. Podvalnyy, Alexander O. Chizhov, Alexander I. Zinin, Leonid O. Kononov
      Rapid and simple synthesis of oligosaccharides related to one of the terminal motifs of mycobacterial lipoarabinomannan is described. An array of homologous linear α(1 → 5)-linked oligoarabinofuranosides with 4-(2-chloroethoxy)phenyl aglycon and selectively unprotected 5-OH group at the non-reducing end was obtained by oligomerization of 3-O-benzoyl β-D-arabinofuranose 1,2,5-orthobenzoate. Subsequent introduction of β(1 → 2)-linked arabinofuranose disaccharide moiety by step-wise glycosylation furnished the target oligosaccharides which were conjugated with bovine serum albumin.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Synthetic multivalent ligands for cholera & cholera-like toxins:
           Protected cyclic neoglycopeptides
    • Abstract: Publication date: 5 August 2016
      Source:Carbohydrate Research, Volume 431
      Author(s): Vajinder Kumar, Narender Yadav, K.P. Ravindranathan Kartha
      Synthesis of a set of novel glycopeptide analogues as potential cholera/cholera-like toxin inhibitors in their protected form is described. They include di-, tri-, tetra- and pentavalent scaffolds. The synthetic steps were achieved using a combination of solvent-free mechanochemical as well as the conventional solution-phase reactions. During the conventional DIC-HOBt-mediated peptide coupling followed for the preparation of certain glycopeptide analogues an interesting in situ Fmoc deprotection was observed which has been demonstrated to hold potential for synthesiszing glycopeptides/neoglycopeptides with extended polyamide chains.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Structural and binding properties of laminarin revealed by analytical
           ultracentrifugation and calorimetric analyses
    • Abstract: Publication date: 5 August 2016
      Source:Carbohydrate Research, Volume 431
      Author(s): Masayuki Oda, Yoichi Tanabe, Masanori Noda, Satomi Inaba, Elena Krayukhina, Harumi Fukada, Susumu Uchiyama
      One of the β-1,3-glucans, laminarin, has been widely used as a substrate for enzymes including endo-1,3-β-glucanase. To obtain quantitative information about the molecular interaction between laminarin and endo-1,3-β-glucanase, the structural properties of laminarin should be determined. The results from pioneering work using analytical ultracentrifugation for carbohydrate analysis showed that laminarin from Laminaria digitata predominantly exists as a single-chain species with approximately 5% of triple-helical species. Differential scanning calorimetry experiments did not show a peak assignable to the transition from triple-helix to single-chain, supporting the notion that a large proportion of laminarin is the single-chain species. The interaction of laminarin with an inactive variant of endo-1,3-β-glucanase from Cellulosimicrobium cellulans, E119A, was quantitatively analyzed using isothermal titration calorimetry. The binding was enthalpically driven and the binding affinity was approximately 106 M−1. The results from binding stoichiometric analysis indicated that on average, E119A binds to laminarin in a 2:1 ratio. This seems to be reasonable, because laminarin mainly exists as a monomer, the apparent molecular mass of laminarin is 3.6 kDa, and E119A would have substrate-binding subsites corresponding to 6 glucose units. The analytical ultracentrifugation experiments could detect different complex species of laminarin and endo-1,3-β-glucanase.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Structural characterization of the O-polysaccharide isolated from
           Franconibacter helveticus LMG23732T
    • Abstract: Publication date: 5 August 2016
      Source:Carbohydrate Research, Volume 431
      Author(s): Sylwia Szulta, Małgorzata Czerwicka, Stephen J. Forsythe, Karolina Ossowska, Halina Dziadziuszko, Zbigniew Kaczyński
      The bacterial strain Franconibacter helveticus LMG 23732T was previously misidentified as the neonatal pathogen Cronobacter zurichensis. O-polysaccharide (OPS) is a part of lipopolysaccharide (LPS), which is an important cell envelope compound of Gram-negative bacteria. OPS isolated from the bacterium Franconibacter helveticus LMG23732T was characterized by chemical analyses as well as 1D and 2D NMR experiments. Compositional analyses indicated the presence of glucose and unusual 6-deoxy sugar - 6-deoxy-talose (6-dTal). The studied strain produced OPS, which consists of 6-l-dTalp in main chain and terminal d-Glcp as a branch: This is the first structural determination of the OPS isolated from genus Franconibacter.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • An efficient method for the synthesis of pyranoid glycals
    • Abstract: Publication date: 5 August 2016
      Source:Carbohydrate Research, Volume 431
      Author(s): Heshan Chen, Ting Xian, Wan Zhang, Wenshuai Si, Xiaosheng Luo, Bo Zhang, Meiyu Zhang, Zhongfu Wang, Jianbo Zhang
      A simple and efficient procedure was designed for the preparation of pyranoid glycals. In a novel fashion, a series of protected glycopyranosyl bromides underwent reductive elimination in the presence of zinc dust and ammonium chloride in CH3CN at 30–60 °C. The corresponding glycals were obtained with excellent isolated yields (72–96%) in a short time (20–50 min). Furthermore, the transformation was compatible with different protection patterns and conveniently scalable (86% for 45 g acetobromoglucose) which made it very applicable in organic synthesis.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Synthesis and antituberculosis activity of the first macrocyclic
           glycoterpenoids comprising glucosamine and diterpenoid isosteviol
    • Abstract: Publication date: 5 August 2016
      Source:Carbohydrate Research, Volume 431
      Author(s): Bulat F. Garifullin, Irina Yu. Strobykina, Radmila R. Sharipova, Marionella A. Kravchenko, Olga V. Andreeva, Olga B. Bazanova, Vladimir E. Kataev
      The first macrocyclic glycoterpenoids comprising glucosamine and diterpenoid isosteviol moieties were synthesized and evaluated for inhibition activity against Mycobacterium tuberculosis H37Rv.
      Graphical abstract image

      PubDate: 2016-06-15T11:05:10Z
       
  • Synthesis of 6-Phosphofructose Aspartic Acid and Some Related Amadori
           Compounds
    • Abstract: Publication date: Available online 14 May 2016
      Source:Carbohydrate Research
      Author(s): Alexandar L. Hansen, Edward J. Behrman
      We describe the synthesis and characterization of 6-phosphofructose-aspartic acid, an intermediate in the metabolism of fructose-asparagine by Salmonella. We also report improved syntheses of fructose-asparagine itself and of fructose-aspartic acid.
      Graphical abstract image

      PubDate: 2016-05-17T10:15:12Z
       
 
 
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