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  Subjects -> CHEMISTRY (Total: 823 journals)
    - ANALYTICAL CHEMISTRY (49 journals)
    - CHEMISTRY (570 journals)
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    - ELECTROCHEMISTRY (26 journals)
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CHEMISTRY (570 journals)                  1 2 3 4 5 6 | Last

2D Materials     Hybrid Journal   (Followers: 4)
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: 25)
ACS Chemical Neuroscience     Full-text available via subscription   (Followers: 13)
ACS Combinatorial Science     Full-text available via subscription   (Followers: 8)
ACS Macro Letters     Full-text available via subscription   (Followers: 20)
ACS Medicinal Chemistry Letters     Full-text available via subscription   (Followers: 25)
ACS Nano     Full-text available via subscription   (Followers: 361)
ACS Photonics     Full-text available via subscription   (Followers: 6)
ACS Synthetic Biology     Full-text available via subscription   (Followers: 11)
Acta Chemica Iasi     Open Access  
Acta Chimica Sinica     Full-text available via subscription  
Acta Chimica Slovaca     Open Access   (Followers: 6)
Acta Chromatographica     Full-text available via subscription   (Followers: 10)
Acta Facultatis Medicae Naissensis     Open Access   (Followers: 1)
Acta Metallurgica Sinica (English Letters)     Hybrid Journal   (Followers: 5)
adhäsion KLEBEN & DICHTEN     Hybrid Journal   (Followers: 4)
Adhesion Adhesives & Sealants     Hybrid Journal   (Followers: 5)
Adsorption Science & Technology     Full-text available via subscription   (Followers: 10)
Advanced Functional Materials     Hybrid Journal   (Followers: 39)
Advances in Chemical Engineering and Science     Open Access   (Followers: 23)
Advances in Chemical Science     Open Access   (Followers: 9)
Advances in Colloid and Interface Science     Full-text available via subscription   (Followers: 15)
Advances in Drug Research     Full-text available via subscription   (Followers: 17)
Advances in Enzyme Research     Open Access  
Advances in Fluorine Science     Full-text available via subscription   (Followers: 7)
Advances in Fuel Cells     Full-text available via subscription   (Followers: 13)
Advances in Heterocyclic Chemistry     Full-text available via subscription   (Followers: 8)
Advances in Materials Physics and Chemistry     Open Access   (Followers: 16)
Advances in Nanoparticles     Open Access   (Followers: 12)
Advances in Organometallic Chemistry     Full-text available via subscription   (Followers: 9)
Advances in Polymer Science     Hybrid Journal   (Followers: 39)
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: 5)
Afrique Science : Revue Internationale des Sciences et Technologie     Open Access   (Followers: 1)
Agrokémia és Talajtan     Full-text available via subscription   (Followers: 1)
Alchemy     Open Access   (Followers: 3)
Alkaloids: Chemical and Biological Perspectives     Full-text available via subscription   (Followers: 5)
AMB Express     Open Access  
Ambix     Hybrid Journal   (Followers: 2)
American Journal of Applied Sciences     Open Access   (Followers: 31)
American Journal of Biochemistry and Biotechnology     Open Access   (Followers: 216)
American Journal of Biochemistry and Molecular Biology     Open Access   (Followers: 12)
American Journal of Chemistry     Open Access   (Followers: 18)
American Journal of Plant Physiology     Open Access   (Followers: 10)
American Mineralogist     Full-text available via subscription   (Followers: 7)
Analyst     Full-text available via subscription   (Followers: 38)
Angewandte Chemie     Hybrid Journal   (Followers: 18)
Angewandte Chemie International Edition     Hybrid Journal   (Followers: 275)
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: 11)
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: 21)
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   (Followers: 1)
Avances en Quimica     Open Access   (Followers: 1)
Biochemical Pharmacology     Hybrid Journal   (Followers: 7)
Biochemistry     Full-text available via subscription   (Followers: 274)
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)
Bioinspired Materials     Open Access  
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: 14)
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: 2)
Bulletin of the Chemical Society of Japan     Full-text available via subscription   (Followers: 13)
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: 11)
Carbon     Hybrid Journal   (Followers: 55)
Catalysis for Sustainable Energy     Open Access   (Followers: 2)
Catalysis Reviews: Science and Engineering     Hybrid Journal   (Followers: 6)
Catalysis Science and Technology     Free   (Followers: 4)
Catalysis Surveys from Asia     Hybrid Journal   (Followers: 4)

        1 2 3 4 5 6 | Last

Journal Cover   Carbohydrate Research
  [SJR: 0.654]   [H-I: 83]   [13 followers]  Follow
    
   Hybrid Journal Hybrid journal (It can contain Open Access articles)
   ISSN (Print) 0008-6215 - ISSN (Online) 0008-6215
   Published by Elsevier Homepage  [2588 journals]
  • Structure of a new pseudaminic acid-containing capsular polysaccharide of
           Acinetobacter baumannii LUH5550 having the KL42 capsule biosynthesis locus
           
    • Abstract: Publication date: 30 April 2015
      Source:Carbohydrate Research, Volume 407
      Author(s): Sof'ya N. Senchenkova , Anastasiya V. Popova , Alexander S. Shashkov , Mikhail M. Shneider , Zhu Mei , Nikolay P. Arbatsky , Bin Liu , Konstantin A. Miroshnikov , Nikolay V. Volozhantsev , Yuriy A. Knirel
      The capsular polysaccharide from Acinetobacter baumannii LUH5550 was studied by 1D and 2D 1H and 13C NMR spectroscopy. The following structure of the branched trisaccharide repeating unit was established: where Pse5Ac7RHb indicates 5-acetamido-3,5,7,9-tetradeoxy-7-[(R)-3-hydroxybutanoylamino]-l-glycero-l-manno-non-2-ulosonic acid. The genes in the capsule biosynthesis locus designated KL42 are consistent with the structure established.
      Graphical abstract image

      PubDate: 2015-03-16T13:03:57Z
       
  • C-glycosphingolipid precursors via iodocyclization of homoallyic
           trichloroacetimidates
    • Abstract: Publication date: 30 April 2015
      Source:Carbohydrate Research, Volume 407
      Author(s): Ahmad S. Altiti , David R. Mootoo
      The iodocyclization of homoallylic trichloroacetimidates derived from α-C-allyl galactoside were investigated. In line with the stereochemical trend observed for less substituted non-glycosylated frameworks, E and Z substrates delivered stereoselectively the 1,3-anti and 1,3-syn amino alcohol motifs, respectively. These products are advanced precursors to C-glycosides of the potent immunostimulatory glycolipid KRN7000.
      Graphical abstract image

      PubDate: 2015-03-16T13:03:57Z
       
  • Mechanochemical click reaction as a tool for making carbohydrate-based
           triazole-linked self-assembling materials (CTSAMs)
    • Abstract: Publication date: 30 April 2015
      Source:Carbohydrate Research, Volume 407
      Author(s): Mohit Tyagi , Nikhil Taxak , Prasad V. Bharatam , Hemraj Nandanwar , K.P. Ravindranathan Kartha
      Various glycosides in which glycosylated triazole residues are anchored on to a central phenyl ring have been prepared under green reaction conditions by a solvent-free mechanochemical method. Some of the glycosides exhibited the ability to form gels when in contact with long chain hydrocarbons, e.g. hexane, heptane and octane, and this property was phase-selective. Thus, from a mixture of hexane–water, the compounds preferably absorbed the alkane to form a gel. The gelation ability was found to increase with an increasing number of substituents on the phenyl ring but only up to tetra-substitution. The hexa-substituted phenyl derivative did not swell in the hydrocarbon solvents investigated. The spontaneous self-assembling properties of these compounds in hexane have been investigated by transmission electron microscopy (TEM). Molecular modelling was used to optimize the structural geometry of these carbohydrate-based triazole-linked self-assembling materials (CTSAMs) and to rationalize their behaviour.
      Graphical abstract image

      PubDate: 2015-03-16T13:03:57Z
       
  • Classification of a Proteus penneri clinical isolate with a unique
           O-antigen structure to a new Proteus serogroup, O80
    • Abstract: Publication date: 30 April 2015
      Source:Carbohydrate Research, Volume 407
      Author(s): Małgorzata Siwińska , Evgeniya A. Levina , Olga G. Ovchinnikova , Dominika Drzewiecka , Alexander S. Shashkov , Antoni Różalski , Yuriy A. Knirel
      Proteus penneri is an opportunistic pathogen, which may cause severe diseases, most frequently urinary tract infections in immunocompromised patients. P. penneri Br 114 exhibiting a good swarming growth ability as an S-form strain was isolated from a wound of a patient in Łódź, Poland. Serological studies using ELISA and Western blotting and chemical analyses along with 1H and 13C NMR spectroscopy showed that the O-antigen (O-polysaccharide) of this strain is unique among the known Proteus serotypes O1–O79. It possesses a linear pentasaccharide repeating unit containing a partially O-acetylated amide of d-glucuronic acid (GlcA) with l-serine having the following structure: These data are a basis for creating a new Proteus serogroup, O80, so far represented by the single Br 114 isolate. The O80 is the 21st O-serogroup containing P. penneri strains and the fourth serogroup based on Proteus spp. clinical isolates from Łódź, Poland.
      Graphical abstract image

      PubDate: 2015-03-13T06:59:38Z
       
  • A recyclable heavy fluorous tag carrying an allyl alcohol pendant group:
           design and evaluation toward applications in synthetic carbohydrate
           chemistry
    • Abstract: Publication date: 30 April 2015
      Source:Carbohydrate Research, Volume 407
      Author(s): Kazuo Fukuda , Mami Tojino , Kohtaro Goto , Hirofumi Dohi , Yoshihiro Nishida , Mamoru Mizuno
      Toward applications in synthetic carbohydrate chemistry, we converted our previous acid-resistant heavy fluorous tag [(Rf)3C–CH2–OH, 1] to allyl alcohol derivatives [(Rf)3C–CH2–O–(CH2) n –CHCH–CH2–OH, 3 (n=1) or 4 (n=3)] by means of olefin cross metathesis. They were then subjected to β-glycosylation reactions by using a series of glycosyl donors, including glycosyl bromide and trichloroacetimidates. The terminal OH group in 3 and 4 was found to be β-glycosylated in moderate yield when 2,3,4,6-tetra-O-benzoyl-d-galactosyl trichloroacetimidate was used as the glycosyl donor. Upon a detachment reaction using Pd(PPh3)4, the initial heavy fluorous tag 1 was recovered in high yield (>90%) together with 1-hydroxy sugar, indicating that not only the allyl ether linkage in the glycosides but also the internal di-alkyl ether linkage in 4 be cleaved by the action of the Pd-catalyst enabling long-range olefin transmigration. Potential utility was demonstrated by using the tetra-O-benzoyl-β-d-galactosylated derivative of 3 in a series of deprotection, protection and glycosylation reactions, which were conductible in high yields without using chromatographic purification process. These findings prompt us to propose a general scheme in which the acid-resistant heavy fluorous compound 1 is applied as a recyclable tag in synthetic carbohydrate chemistry.
      Graphical abstract image

      PubDate: 2015-03-13T06:59:38Z
       
  • Ferrier rearrangement promoted by an electrochemically generated zirconium
           catalyst
    • Abstract: Publication date: 30 April 2015
      Source:Carbohydrate Research, Volume 407
      Author(s): Dragana Stevanović , Anka Pejović , Ivan Damljanović , Aleksandra Minić , Goran A. Bogdanović , Mirjana Vukićević , Niko S. Radulović , Rastko D. Vukićević
      In situ generated zirconium catalyst from a sacrificial zirconium anode was successfully applied to promote Ferrier rearrangement of 3,4,5-tri-O-acetyl-d-glucal and 6-deoxy-3,4-di-O-acetyl-l-glucal (3,4-di-O-acetyl-l-rhamnal) in the presence of three thiols and eleven thiophenols as nucleophiles. A simple constant current electrolysis (20 mA, 0.4 F mol−1) of an acetonitrile solution of lithium perchlorate (0.1 M) containing the corresponding glycal and S-nucleophiles, using a zirconium anode and a platinum cathode resulted in the successful synthesis of the corresponding 2,3-unsaturated peracetylated thioglycosides (with an average anomer ratio α/β=4.129 in the case of peracetylated d-glucal and 8.740 in the case of l-rhamnal). The same procedure proved to be appropriate in synthesizing dihydropyran derivatives (‘C-glycosides’) using allyltrimethylsilane as the nucleophile (only ‘α-anomers’ were obtained). All new compounds were fully characterized by spectral data, whereas single-crystal X-ray analysis was performed for two thioglycosides.
      Graphical abstract image

      PubDate: 2015-03-09T13:00:35Z
       
  • Synthesis of novel Schiff base ligands from gluco- and galactochloraloses
           for the Cu(II) catalyzed asymmetric Henry reaction
    • Abstract: Publication date: 30 April 2015
      Source:Carbohydrate Research, Volume 407
      Author(s): Sevda Alkan , Fatma Ç. Telli , Yeşim Salman , Stephen T. Astley
      A series of chiral Schiff base ligands has been prepared using aminochloralose derivatives of glucose and galactose. These ligands were used as catalysts in the asymmetric Henry reaction in the presence of Cu(II) ions giving yields of up to 95%. An interesting solvent dependency on enantiomeric control was observed with the best enantiomeric excesses (up to 91%) being obtained in the presence of water.
      Graphical abstract image

      PubDate: 2015-03-09T13:00:35Z
       
  • Spectroscopic and structural studies on lactose species in aqueous
           solution combining the HATR and Raman spectra with SCRF calculations
    • Abstract: Publication date: 30 April 2015
      Source:Carbohydrate Research, Volume 407
      Author(s): María Jimena Márquez , Alicia Beatriz Brizuela , Lilian Davies , Silvia Antonia Brandán
      In this work, the α and β isomers, the α-lactose monohydrate and dihydrate and the dimeric species of lactose were studied from the spectroscopic point of view in gas and aqueous solution phases combining the infrared, Horizontal Attenuated Total Reflectance (HATR) and Raman spectra with the density functional theory (DFT) calculations. Aqueous saturated solutions of α-lactose monohydrate and solutions at different molar concentrations of α-lactose monohydrate in water were completely characterized by infrared, HATR and Raman spectroscopies. For all the species in solution, the solvent effects were studied using the solvation polarizable continuum (PCM) and solvation (SM) models and, then, their corresponding solvation energies were predicted. The vibrational spectra of those species in aqueous solution were completely assigned by employing the Scaled Quantum Mechanics Force Field (SQMFF) methodology and the self-consistent reaction field (SCRF) calculations. The stabilities of all those species were studied by using the natural bond orbital (NBO), and atoms in molecules (AIM) calculations.
      Graphical abstract image

      PubDate: 2015-03-09T13:00:35Z
       
  • Fragment profiling of low molecular weight heparins using reversed phase
           ion pair liquid chromatography-electrospray mass spectrometry
    • Abstract: Publication date: 30 April 2015
      Source:Carbohydrate Research, Volume 407
      Author(s): Xiaohui Xu , Daoyuan Li , Lequan Chi , Xuzhao Du , Xue Bai , Lianli Chi
      Low molecular weight heparins (LMWHs) are linear and highly charged carbohydrate polymers prepared by chemical or enzymatic depolymerization of heparin. Compared to unfractionated heparin (UFH), LMWHs are prevalently used as clinical anticoagulant drugs due to their lower side effects and better bioavailability. The work presented herein provides a rapid and powerful fragment mapping method for structural characterization of LMWHs. The chain fragments of two types of LMWHs, enoxaparin and nadroparin, were generated by controlled enzymatic digestion with each of heparinase I (Hep I, Enzyme Commission (EC) # 4.2.2.7), heparinase II (Hep II, no EC # assigned) and heparinase III (Hep III, EC # 4.2.2.8). Reversed phase ion pair high performance liquid chromatography (RPIP-HPLC) coupled with electrospray ion trap time-of-flight mass spectrometry (ESI-IT-TOF-MS) was used to profile the oligosaccharide chains ranging from disaccharides to decasaccharides. A database containing all theoretical structural compositions was established to assist the mass spectra interpretation. The six digests derived by three enzymes from two types of LMWHs exhibited distinguishable fingerprinting patterns. And a total of 94 enoxaparin fragments and 109 nadroparin fragments were detected and identified. Besides the common LMWH oligosaccharides, many components containing characteristic LMWH structures such as saturated l-idopyranosuronic acid, 2,5-anhydro-d-mannitol, 1,6-anhydro-d-aminopyranose, as well as odd number oligosaccharides were also revealed. Quantitative comparison of major components derived from innovator and generic nadroparin products was presented. This approach to profile LMWHs' fragments offers a highly reproducible, high resolution and information-rich tool for evaluating the quality of this category of anticoagulant drugs or comparing structural similarities among samples from various sources.
      Graphical abstract image

      PubDate: 2015-03-09T13:00:35Z
       
  • Isolation and characterization of feruloylated arabinoxylan
           oligosaccharides from the perennial cereal grain intermediate wheat grass
           (Thinopyrum intermedium)
    • Abstract: Publication date: 30 April 2015
      Source:Carbohydrate Research, Volume 407
      Author(s): Rachel R. Schendel , Andreas Becker , Catrin E. Tyl , Mirko Bunzel
      In comparison to the annual grain crops dominating current agricultural production, perennial grain species require fewer chemical and energy inputs and improve soil health and erosion control. The possibility for producing sustainable grain harvests from marginal land areas is motivating research initiatives to integrate perennial grains into commercial cropping and food processing systems. In this study, the feruloylated arabinoxylans from intermediate wheat grass (Thinopyrum intermedium, IWG), a promising perennial grain candidate in agronomic screening studies, were investigated. Insoluble fiber isolated from IWG whole grain flour was subjected to either mildly acidic (50 mM TFA, 100 °C, 2 h) or enzymatic (Driselase) hydrolysis. The liberated feruloylated arabinoxylan oligosaccharides were concentrated with Amberlite XAD-2, separated with gel chromatography (Sephadex LH-20, water), and purified with reversed-phase HPLC (C18, water-MeOH gradient). Thirteen feruloylated oligosaccharides were isolated (including eight structures described for the first time) and identified by LC-ESI-MS and NMR. Linkage-type analysis via methylation analysis, as well as the monosaccharide and phenolic acid profiles of the IWG insoluble fiber were also determined. IWG feruloylated arabinoxylans have a relatively simple structure with only short feruloylated side chains, a lower backbone substitution rate than annual rye and wheat varieties, and a moderate phenolic acid content.
      Graphical abstract image

      PubDate: 2015-03-09T13:00:35Z
       
  • Hydrolysis of wheat flour arabinoxylan, acid-debranched wheat flour
           arabinoxylan and arabino-xylo-oligosaccharides by β-xylanase,
           α-l-arabinofuranosidase and β-xylosidase
    • Abstract: Publication date: 30 April 2015
      Source:Carbohydrate Research, Volume 407
      Author(s): Barry V. McCleary , Vincent A. McKie , Anna Draga , Edward Rooney , David Mangan , Jennifer Larkin
      A range of α-l-arabinofuranosyl-(1-4)-β-d-xylo-oligosaccharides (AXOS) were produced by hydrolysis of wheat flour arabinoxylan (WAX) and acid debranched arabinoxylan (ADWAX), in the presence and absence of an AXH-d3 α-l-arabinofuranosidase, by several GH10 and GH11 β-xylanases. The structures of the oligosaccharides were characterised by GC-MS and NMR and by hydrolysis by a range of α-l-arabinofuranosidases and β-xylosidase. The AXOS were purified and used to characterise the action patterns of the specific α-l-arabinofuranosidases. These enzymes, in combination with either Cellvibrio mixtus or Neocallimastix patriciarum β-xylanase, were used to produce elevated levels of specific AXOS on hydrolysis of WAX, such as 32-α-l-Araf-(1-4)-β-d-xylobiose (A3X), 23-α-l-Araf-(1-4)-β-d-xylotriose (A2XX), 33-α-l-Araf-(1-4)-β-d-xylotriose (A3XX), 22-α-l-Araf-(1-4)-β-d-xylotriose (XA2X), 32-α-l-Araf (1-4)-β-d-xylotriose (XA3X), 23-α-l-Araf-(1-4)-β-d-xylotetraose (XA2XX), 33-α-l-Araf-(1-4)-β-d-xylotetraose (XA3XX), 23,33-di-α-l-Araf-(1-4)-β-d-xylotriose (A2+3XX), 23,33-di-α-l-Araf-(1-4)-β-d-xylotetraose (XA2+3XX), 24,34-di-α-l-Araf-(1-4)-β-d-xylopentaose (XA2+3XXX) and 33,34-di-α-l-Araf-(1-4)-β-d-xylopentaose (XA3A3XX), many of which have not previously been produced in sufficient quantities to allow their use as substrates in further enzymic studies. For A2,3XX, yields of approximately 16% of the starting material (wheat arabinoxylan) have been achieved. Mixtures of the α-l-arabinofuranosidases, with specific action on AXOS, have been combined with β-xylosidase and β-xylanase to obtain an optimal mixture for hydrolysis of arabinoxylan to l-arabinose and d-xylose.
      Graphical abstract image

      PubDate: 2015-03-09T13:00:35Z
       
  • Isolation and characterization of unhydrolyzed oligosaccharides from
           switchgrass (Panicum virgatum, L.) xylan after exhaustive enzymatic
           treatment with commercial enzyme preparations
    • Abstract: Publication date: 30 April 2015
      Source:Carbohydrate Research, Volume 407
      Author(s): Michael J. Bowman , Bruce S. Dien , Karl E. Vermillion , Jeffrey A. Mertens
      Switchgrass (Panicum virgatum, L.) is a potential renewable source of carbohydrates for use in microbial conversion to biofuels. Xylan comprises approximately 30% of the switchgrass cell wall. To understand the limitations of commercial enzyme mixtures, alkali-extracted, isolated switchgrass xylan was hydrolyzed by the action of two commercial enzyme cocktails, in the presence and absence of an additional α-arabinofuranosidase enzyme. The two most abundant enzymatic digestion products from each commercial enzyme treatment were separated and characterized by LC-MS n , linkage analysis, and NMR. The most abundant oligosaccharide from each commercial cocktail was susceptible to hydrolysis when supplemented with a GH62 α-arabinofuranosidase enzyme; further characterization confirmed the presence of (1→3)-α-arabinose linkages. These results demonstrate the lack of the required selectivity for arabinose-containing substrates in the commercial enzyme preparations tested. One product from each condition remained intact and was found to contain (1→2)-β-xylose-(1→3)-α-arabinose side chains; this linkage acts as a source of oligosaccharide recalcitrance.
      Graphical abstract image

      PubDate: 2015-03-09T13:00:35Z
       
  • Characteristics of mannosylerythritol lipids and their environmental
           potential
    • Abstract: Publication date: 30 April 2015
      Source:Carbohydrate Research, Volume 407
      Author(s): Mingda Yu , Zhifeng Liu , Guangming Zeng , Hua Zhong , Yang Liu , Yongbing Jiang , Min Li , Xiaoxiao He , Yan He
      Mannosylerythritol lipids (MELs) are promising biosurfactants containing two glycosyl derivatives and various fatty acids, which are mainly secreted by Pseudozyma as well as Ustilago. In this review, the latest research is demonstrated on production conditions, structural diversity, self-assembling properties and versatile biochemical functions of MELs. The genetic study and synthetic pathways, which mainly influence the type and yield of MELs production. Due to the excellent surface activity, biocompatibility and restorative function, MELs can be used in enviornmental industry, which has not been widely noted. In this paper, the current status of research on enviornmental potential of MELs has been discussed including petroleum degradation, bioconversion of chemical wastes and enhanced bioremediation of amphiphilic wastes.
      Graphical abstract image

      PubDate: 2015-03-09T13:00:35Z
       
  • Kinetic characterization of Aspergillus niger chitinase CfcI using a
           HPAEC-PAD method for native chitin oligosaccharides
    • Abstract: Publication date: 30 April 2015
      Source:Carbohydrate Research, Volume 407
      Author(s): Jolanda M. van Munster , Peter Sanders , Geralt A. ten Kate , Lubbert Dijkhuizen , Marc J.E.C. van der Maarel
      The abundant polymer chitin can be degraded by chitinases (EC 3.2.1.14) and β-N-acetyl-hexosaminidases (EC 3.2.1.52) to oligosaccharides and N-acetyl-glucosamine (GlcNAc) monomers. Kinetic characterization of these enzymes requires product quantification by an assay method with a low detection limit, preferably compatible with the use of native, non-labeled substrates. Here we report a quantitative HPAEC-PAD method that allows fast separation of chitin oligosaccharides (COS) ranging from (GlcNac)1–6 at detection limits of 1–3 pmol and a linear range of 5–250 pmol. Quantification under intra- and interday precision conditions was performed with 2.1–5.4% relative standard deviation (RSD) and 1.2–10.3% RSD, respectively. This method was successfully used for the determination of the kinetic parameters of the Aspergillus niger chitinase CfcI with native COS. CfcI was recently shown to release GlcNAc from the reducing end of COS, a new activity for fungal chitinases. A Carbohydrate Binding Module of family 18 (CBM18) is inserted in the CfcI catalytic domain. Site directed mutagenesis was used to assess the functionality of this CfcI-CBM18: four of its key amino acids were replaced by glycine residues, yielding CfcISYNF. Comparison of the kinetic parameters of CfcI and CfcISYNF confirmed that this CBM18 is functionally involved in catalysis.
      Graphical abstract image

      PubDate: 2015-03-09T13:00:35Z
       
  • Structure of a zwitterionic O-polysaccharide from Photorhabdus temperata
           subsp. cinerea 3240
    • Abstract: Publication date: 30 April 2015
      Source:Carbohydrate Research, Volume 407
      Author(s): Anna N. Kondakova , Nadezhda A. Kirsheva , Nikolay P. Arbatsky , Rima Z. Shaikhutdinova , Alexander S. Shashkov , Sergey A. Ivanov , Andrey P. Anisimov , Yuriy A. Knirel
      A phosphorylated O-polysaccharide was isolated from the lipopolysaccharide of an entomopathogenic bacterium Photorhabdus temperata subsp. cinerea 3240 and studied by sugar analysis, dephosphorylation, and 1H and 13C NMR spectroscopy. The following structure of the linear trisaccharide repeating unit of the O-polysaccharide was established: →3)-β-d-GalpNAc4PEtN-(1→4)-β-d-GlcpA-(1→3)-β-d-FucpNAc4N-(1→ where GlcA indicates glucuronic acid, FucNAc4N 2-acetamido-4-amino-2,4,6-trideoxygalactose, and PEtN 2-aminoethyl phosphate.
      Graphical abstract image

      PubDate: 2015-03-09T13:00:35Z
       
  • Mass spectrometry-based method to investigate the natural selectivity of
           sucrose as the sugar transport form for plants
    • Abstract: Publication date: 30 April 2015
      Source:Carbohydrate Research, Volume 407
      Author(s): Hang Yuan , Yile Wu , Wu Liu , Yan Liu , Xiang Gao , Jinming Lin , Yufen Zhao
      Sucrose is the carbon skeletons and energy vector for plants, which is important for plants growth. Among thousands of disaccharides in Nature, why chose sucrose for plants? In this paper, we analyzed the intrinsic structural characteristics of four sucrose isomers with different glycosidic linkage by mass spectrometry (MS) technique. Our results show that sucrose has the most labile glycosidic bond compared with other three isomers, which is helpful for releasing glucose and fructose unit. Besides, sucrose has the most stable integral structure, which is hard to dehydrate and degrade into fragments through losing one or three even four-carbon units, just as its three isomers. In other words, sucrose is more easily holds an integral structure during the transport process, whenever it is necessary, and sucrose can be cleaved into glucose and fructose easily. Besides, we also investigate the internal relationship of sucrose with K+ by tandem mass spectrometry and viscosity measurement. The related results have shown that the K+ can stabilize sucrose to a greater extent than the Na+. Furthermore, under the same conditions, K+ ions reduce the viscosity of sucrose–water system much more than Na+. These results suggest that K+ is a better co-transporter for sucrose. Of course, the transport of sucrose in plants is a very complicated process, which is involved in many proteins. This paper directly accounts for the basic structure feature of sucrose, and the results discovered could provide the novel insight for the answer why Nature chose sucrose for plants.
      Graphical abstract image

      PubDate: 2015-03-09T13:00:35Z
       
  • Nuclear magnetic resonance studies of the interactions between the organic
           germanium compound Ge-132 and saccharides
    • Abstract: Publication date: 30 April 2015
      Source:Carbohydrate Research, Volume 407
      Author(s): Yasuhiro Shimada , Katsuyuki Sato , Yoshihiko Tokuji , Takashi Nakamura
      Poly-trans-[(2-carboxyethyl)germasesquioxane], Ge-132, is a water-soluble organic germanium compound with many reported physiological functions. The hydrolysate of Ge-132, 3-(trihydroxygermyl)propanoic acid, can interact with diol compounds; therefore, it can possibly interact with diol-containing sugar compounds, which have important physiological functions in sugar chains, glycoproteins, and glucolipids. In this study, we examined the interaction between sodium 3-(trihydroxygermyl)propanoate and monosaccharides using nuclear magnetic resonance. When 1,4-anhydroerythritol was mixed with sodium 3-(trihydroxygermyl)propanoate, a pattern of signals different from that obtained for each solute alone was observed. Some signals were broader, and novel signals with different chemical shifts appeared to originate from complex formation. Spectral observations for sodium 3-(trihydroxygermyl)propanoate and the sugar isomers of glucose and fructose indicated that sodium 3-(trihydroxygermyl)propanoate has a higher affinity for fructose (a ketose) than glucose (an aldose). Moreover, the β-furanosyl conformation of fructose was the structure that interacted most with sodium 3-(trihydroxygermyl)propanoate. These results demonstrate the ability of aqueous Ge-132 to form complexes with the cis-diol structures of saccharides. Thus, interactions among 3-(trihydroxygermyl)propanoic acid and the important biological sugar compounds might be implicated in the physiological function of Ge-132.
      Graphical abstract image

      PubDate: 2015-03-09T13:00:35Z
       
  • Room-temperature ionic liquids enhanced green synthesis of β-glycosyl
           1-ester
    • Abstract: Publication date: 30 April 2015
      Source:Carbohydrate Research, Volume 407
      Author(s): Yanli Cui , Minghan Xu , Weirong Yao , Jianwei Mao
      We herein report an efficient synthesis of β-glycosyl 1-ester in room-temperature ionic liquids (RTILs) promoted via silver salt and quaternary ammonium salt (PTC) with good or excellent yields. All products were isolated exclusively as the β-anomers. Four different RTILs, eight metal salts and four quaternary ammonium salts were screened in the glycosylation reaction. The synergistic effect of C6mim·OTf, Ag2O and tetrabutylammonium iodine gave the best results. Their promotion to the system was integral. Thorough study provided insight into the catalytic activity of ionic liquid structure, metal salts and quaternary ammonium salt to these reactions. It is worth mentioning that the yield of aliphatic compound 2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl butyrate (3l) was highly improved when using C6mim·OTf as solvent compared with the normal volatile solvents under the same catalysts. This green approach has been proved to be practical and compatible with a wide range from aliphatic to aromatic substrates.
      Graphical abstract image

      PubDate: 2015-03-09T13:00:35Z
       
  • Structural studies of O-polysaccharide isolated from Cronobacter sakazakii
           Sequence Type 12 from a case of neonatal necrotizing enterocolitis
    • Abstract: Publication date: 30 April 2015
      Source:Carbohydrate Research, Volume 407
      Author(s): Kinga Marszewska , Małgorzata Czerwicka , Stephen J. Forsythe , Karolina Ossowska , Halina Dziadziuszko , Zbigniew Kaczyński
      The O-polysaccharide (OPS) of Cronobacter sakazakii NTU 696 (Sequence Type 12) from a case of neonatal necrotizing enterocolitis was isolated from the polysaccharide fraction obtained after lipopolysaccharide (LPS) hydrolysis. Purified OPS was analyzed by NMR spectroscopy (1H, COSY, TOCSY, NOESY, HSQC, HSQC-TOCSY and HMBC experiments) and chemical methods. Obtained monosaccharide derivatives analyzed by gas chromatography and gas chromatography-mass spectrometry allowed the identification of six sugar components. Performed experiments enabled to establish a structure of the OPS repeating unit of C. sakazakii NTU 696, as:
      Graphical abstract image

      PubDate: 2015-03-09T13:00:35Z
       
  • Structure and genetics of the O-antigen of Enterobacter cloacae G3054
           containing di-N-acetylpseudaminic acid
    • Abstract: Publication date: 30 April 2015
      Source:Carbohydrate Research, Volume 407
      Author(s): Andrei V. Perepelov , Min Wang , Andrei V. Filatov , Xi Guo , Alexander S. Shashkov , Lei Wang , Yuriy A. Knirel
      Mild acid degradation of the lipopolysaccharide of Enterobacter cloacae G3054 resulted in the cleavage of the O-polysaccharide at the linkage of residues of 5,7-diacetamido-3,5,7,9-tetradeoxy-l-glycero-l-manno-non-2-ulosonic acid (di-N-acetylpseudaminic acid, Pse5Ac7Ac) in the main chain. The resultant oligosaccharide and an alkali-treated lipopolysaccharide were studied by sugar analysis along with 1H and 13C NMR spectroscopy, and the following structure of the branched pentasaccharide O-unit of the O-polysaccharide was established: The O-antigen gene cluster of E. cloacae G3054 between conserved genes galF and gnd was sequenced. Most genes necessary for the O-antigen synthesis were found in the cluster and their functions were tentatively assigned by comparison with sequences in the available databases.
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      PubDate: 2015-03-09T13:00:35Z
       
  • Synthesis and biotinylation of oligosaccharide fragments of mannosylated
           and 5-deoxy-5-methylthio-xylofuranosylated lipoarabinomannan from
           Mycobacterium tuberculosis
    • Abstract: Publication date: 30 April 2015
      Source:Carbohydrate Research, Volume 407
      Author(s): Pintu Kumar Mandal , Pratik Rajesh Chheda
      The attachment of biotin to a molecule provides a powerful tool in biology. Here, we report an efficient synthesis and biotinylation of mannosylated and 5-deoxy-5-methylthio-xylofuranosylated Lipoarabinomannan from Mycobacterium tuberculosis. Preparation of the oligosaccharides involved the sequential addition of thioglycoside donors with arabinofuranosyl-containing acceptors. Methylthio group was introduced near the end of the synthesis.
      Graphical abstract image

      PubDate: 2015-03-09T13:00:35Z
       
  • Editorial board
    • Abstract: Publication date: 10 April 2015
      Source:Carbohydrate Research, Volume 406




      PubDate: 2015-03-09T13:00:35Z
       
  • Graphical contents list
    • Abstract: Publication date: 10 April 2015
      Source:Carbohydrate Research, Volume 406




      PubDate: 2015-03-09T13:00:35Z
       
  • Synthesis, emulsification and self-assembly properties of sugar-containing
           semifluorinated amphiphiles
    • Abstract: Publication date: 10 April 2015
      Source:Carbohydrate Research, Volume 406
      Author(s): Andrew V. Razgulin , Sandro Mecozzi
      Surfactants with two and three monosaccharide-based heads and a perfluoroalkyl tail have been synthesized. Perfluoroalkyl C3-symmetric triol and C2-symmetric diol were conveniently prepared via Cu-catalyzed azide–alkyne cycloaddition between a fluorous alkyne and tertiary and secondary azides, respectively. Glycosylation of the perfluoroalkyl diol and triol led to orthoester-type structures, which were evaluated for their capacity to stabilize aqueous emulsions of highly fluorinated anesthetics. The self-assembly properties of the tri-sugar amphiphile were examined by transmission electron microscopy.
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      PubDate: 2015-03-09T13:00:35Z
       
  • ‘Click chemistry’ synthesis of
           1-(α-d-mannopyranosyl)-1,2,3-triazoles for inhibition of
           α-mannosidases
    • Abstract: Publication date: 10 April 2015
      Source:Carbohydrate Research, Volume 406
      Author(s): Monika Poláková , Rhiannon Stanton , Iain B.H. Wilson , Ivana Holková , Sergej Šesták , Eva Machová , Zuzana Jandová , Juraj Kóňa
      Three new triazole conjugates derived from d-mannose were synthesized and assayed in in vitro assays to investigate their ability to inhibit α-mannosidase enzymes from the glycoside hydrolase (GH) families 38 and 47. The triazole conjugates were more selective for a GH47 α-mannosidase (Aspergillus saitoi α1,2-mannosidase), showing inhibition at the micromolar level (IC50 values of 50–250 μM), and less potent towards GH38 mannosidases (IC50 values in the range of 0.5–6 mM towards jack bean α-mannosidase or Drosophila melanogaster lysosomal and Golgi α-mannosidases). The highest selectivity ratio [IC50(GH38)/IC50(GH47)] of 100 was exhibited by the phenyltriazole conjugate. To understand structure-activity properties of synthesized compounds, 3-D complexes of inhibitors with α-mannosidases were built using molecular docking calculations.
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      PubDate: 2015-03-09T13:00:35Z
       
  • The application of 2,2,2-trichloroethyl sulfate to the synthesis of
           chondroitin sulfate C and D
    • Abstract: Publication date: 10 April 2015
      Source:Carbohydrate Research, Volume 406
      Author(s): Kenya Matsushita , Tomomi Nakata , Jun-ichi Tamura
      Chondroitin sulfates (CSs) have characteristic bioactivities that depend on sulfation patterns. Chemically synthesized CS oligosaccharides are valuable tools for elucidating the relationship between structures and bioactivities. 2,2,2-Trichloroethyl (TCE) sulfated sugars are highly soluble in nonpolar solvents, which is useful for the synthesis of sulfated oligosaccharides. We herein synthesized CS-C [βGalNAc6S(1–4)βGlcA] (1) and CS-D [βGalNAc6S(1–4)βGlcA2S] (2) disaccharides that possessed sulfate groups by TCE sulfation at O-6 of GalNAc and an additional sulfate group at O-2 of GlcA, respectively. We revealed the superior functionalities of TCE sulfates during the synthesis of CS-C and -D, despite the unwanted side reactions in the acetamido-containing substrate.
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      PubDate: 2015-03-09T13:00:35Z
       
  • Ruthenium catalyzed synthesis of 2,3-unsaturated C-glycosides from glycals
    • Abstract: Publication date: 10 April 2015
      Source:Carbohydrate Research, Volume 406
      Author(s): Batthula Srinivas , Thurpu Raghavender Reddy , Sudhir Kashyap
      A highly efficient and convenient C-glycosylation method was developed using ruthenium(III) chloride for the synthesis of 2,3-unsaturated C-glycosides. Various nucleophiles such as allyl trimethylsilane, triethylsilane, trimethylsilyl cyanide, trimethylsilyl azide and heterocycles such as thiophene and furan reacted smoothly with glycals in the presence of catalytic amount of ruthenium trichloride under mild reaction conditions.
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      PubDate: 2015-03-09T13:00:35Z
       
  • Preparation, spectroscopy and molecular modelling studies of the inclusion
           complex of cordycepin with cyclodextrins
    • Abstract: Publication date: 10 April 2015
      Source:Carbohydrate Research, Volume 406
      Author(s): Jian-Qiang Zhang , Di Wu , Kun-Ming Jiang , Da Zhang , Xi Zheng , Chun-Ping Wan , Hong-You Zhu , Xiao-Guang Xie , Yi Jin , Jun Lin
      The inclusion complexes of cordycepin with cyclodextrins (CDs) were prepared, the resultant complexes were characterised by UV–vis, FTIR, DSC, SEM, XRD, ESI-MS and proton nuclear magnetic resonance spectroscopy (1H NMR). The stoichiometry was established using a Job plot and the inclusion mechanism was clarified using molecular dynamic simulations. Molecular modelling calculations have been carried out to rationalise the experimental findings and predict the stable molecular structure of the inclusion complex. The stability of the inclusion complexes were confirmed by energetic and thermodynamic properties (ΔE, ΔH, ΔG and ΔS) and HOMO, LUMO orbital. The 1:1 binding model of complexes were visually proved by ESI-MS experiment. Our results showed that the purine group of cordycepin molecule was deeply inserted into the cavity of CDs.
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      PubDate: 2015-03-09T13:00:35Z
       
  • Structural features of a novel polysaccharide isolated from a New Zealand
           Maori mushroom Iliodiction cibarium
    • Abstract: Publication date: 10 April 2015
      Source:Carbohydrate Research, Volume 406
      Author(s): Lu Ren , Patrick J.B. Edwards , Conrad O. Perera , Yacine Hemar
      A purified water-soluble fraction (ICP5) of a polysaccharide, isolated from a local Maori mushroom Iliodiction cibarium in New Zealand, was investigated for its structural properties. Size exclusion chromatography and dynamic light scattering showed that ICP5 had a large MW of 1.6×105 Da with a hydrodynamic diameter of 83±8 nm. Particle size measurements also displayed the tendency of ICP5 to aggregate when suspended in water. The results of GC–MS, FTIR and NMR analyses allowed some characteristics of the chemical structure of ICP5 to be determined. GC–MS results showed that ICP5 contained only glucose (81.61%), galactose (12.90%) and mannose (5.49%) monomers. The characterized fragment structures of ICP5 were found to be dominantly consisting of uronic acids, which formed a backbone containing 1,4-β-d-GlcpA. A small amount of unsaturated uronic acid also appeared to be present.
      Graphical abstract image

      PubDate: 2015-03-09T13:00:35Z
       
  • Capsular polysaccharide conformations in pneumococcal serotypes 19F and
           19A
    • Abstract: Publication date: 10 April 2015
      Source:Carbohydrate Research, Volume 406
      Author(s): Michelle M. Kuttel , Graham E. Jackson , Mpho Mafata , Neil Ravenscroft
      Streptococcus pneumoniae is a significant pathogen in children. Although the PCV7 pneumococcal conjugate vaccine has reduced pneumococcal disease, non-vaccine serotype 19A infection has increased, despite expectations of cross-protection from vaccine serotype 19F. Serotype 19A is included in the new PCV13 vaccine, but not in PCV10. In the solution simulations of 19F and 19A oligosaccharide chains reported here, both polysaccharides form unstructured random coils, with inflexible repeat units linked by mobile phosphodiester linkages. However, there are clear conformational differences. In the 19F repeat unit, the rhamnose residue is nearly orthogonal to the other residues, whereas 19A has residues in similar orientations. This finding is corroborated by key inter-residue distances calculated from NMR NOESY experiments. Further, 19F is predominantly in extended conformations, whereas 19A exhibits a high prevalence of tight hairpin bends. These conformational differences may account for a lack of antibody cross-protection between serotypes 19F and 19A.
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      PubDate: 2015-03-09T13:00:35Z
       
  • Quantitative characterization of hydration state and destructuring effect
           of monosaccharides and disaccharides on water hydrogen bond network
    • Abstract: Publication date: 10 April 2015
      Source:Carbohydrate Research, Volume 406
      Author(s): K. Shiraga , T. Suzuki , N. Kondo , J. De Baerdemaeker , Y. Ogawa
      Terahertz time-domain attenuated total reflection measurements of monosaccharide (glucose and fructose) and disaccharide (sucrose and trehalose) solutions from 0.146 M to 1.462 M were performed to evaluate (1) the hydration state and (2) the destructuring effect of saccharide solutes on the hydrogen bond (HB) network. Firstly, the extent of hydration water was determined by the decreased amount of bulk water with picosecond relaxation time that was replaced by that with much longer orientational relaxation time. As a result, we found glucose and trehalose exhibits stronger hydration capacity than fructose and sucrose, respectively, despite of the same number of the hydroxyl groups. For each saccharide, the hydration number tended to decrease with solute concentration. Secondly, the destructuring effect of these saccharide solutes on the HB network of the surrounding bulk water was discussed from the perspective of the fraction of non-hydrogen-bonded (NHB) water isolated from the HB network. We found the fraction of NHB water molecules that are not engaged in the HB network monotonously increased with saccharide concentration, indicating saccharide solutes promote the disruption of the water HB network. However, no noticeable differences were confirmed in the fraction of NHB water between glucose and fructose or between sucrose and trehalose. In contrast to hydration number, the number of NHB water produced by a single saccharide solute was less dependent on solute concentration, and three monosaccharide/disaccharide solutes were found to produce one/two NHB water molecules.
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      PubDate: 2015-03-09T13:00:35Z
       
  • Synthetic study of 3-fluorinated sialic acid derivatives
    • Abstract: Publication date: 10 April 2015
      Source:Carbohydrate Research, Volume 406
      Author(s): Katsuhiko Suzuki , Shusaku Daikoku , Sang-Hyun Son , Yukishige Ito , Osamu Kanie
      Sialic acid derivatives, analogs, and their conjugates are expected to be pharmaceutical candidates such as anti-influenza drugs and also useful probes for investigating the biological role of glycoconjugates. Derivatives of 3-fluorinated sialic acid (3-F-Sia) have been found to be excellent probes in investigating functions and mechanisms of a series of proteins. Here, we describe the syntheses of 3-F-Sia derivatives, which are useful in making biologically important conjugate probes. A practical method for the construction of 3-fluorinated sialosides based on the stereoselective formation of the corresponding anomeric O-trimethylsilyl ether and their nucleophilic attack by an alkyl halide, an allyl halide in particular, was developed. In addition, details of the synthesis of cytidine monophosphate (CMP)-3-F-Sia bearing a fluorescent tag, which has been proven to show dual functions as a substrate of CMP-sialic acid transporter (CST) and an inhibitor of sialyltransferase (STase), are described.
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      PubDate: 2015-03-09T13:00:35Z
       
  • Functional glycolipid-crown-ethers by click chemistry
    • Abstract: Publication date: 10 April 2015
      Source:Carbohydrate Research, Volume 406
      Author(s): Abbas Abdulameer Salman , Mojtaba Tabandeh , Thorsten Heidelberg , Rusnah Syahila Duali Hussen
      A series of glycolipid crown ether analogs was prepared by bis-propargylation of lauryl glycoside followed by subsequent click-coupling with ethylene glycol-based diazides. The triazole-linked macrocycles were obtained in remarkable high yields. While the surfactant assembly was affected by presence of sodium ions, suggesting the formation of complexes, no ion-selectivity was observed for the macrocylic ligands. Computational studies suggest a low but significant cation-binding activity of the macrocycle, involving coordination at both oxygen and nitrogen atoms.
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      PubDate: 2015-03-09T13:00:35Z
       
  • Chemical synthesis of the tetrasaccharide repeating unit of the
           O-polysaccharide isolated from Azospirillum brasilense SR80
    • Abstract: Publication date: 10 April 2015
      Source:Carbohydrate Research, Volume 406
      Author(s): Vikramjit Sarkar , Balaram Mukhopadhyay
      A linear strategy has been developed for the synthesis of the tetrasaccharide repeating unit of the O-polysaccharide from Azospirillum brasilense SR80. Stepwise glycosylation of the rationally protected thioglycoside donors activated by NIS in the presence of La(OTf)3 furnished the target tetrasaccharide. The glycosylation reactions resulted in the formation of the desired linkage with absolute stereoselectivity and afforded the required derivatives in good to excellent yields. The phthalimido group has been used as the precursor of the desired acetamido group to meet the requirement of 1,2-trans glycosidic linkage.
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      PubDate: 2015-03-09T13:00:35Z
       
  • Editorial board
    • Abstract: Publication date: 20 March 2015
      Source:Carbohydrate Research, Volume 405




      PubDate: 2015-03-09T13:00:35Z
       
  • Graphical contents list
    • Abstract: Publication date: 20 March 2015
      Source:Carbohydrate Research, Volume 405




      PubDate: 2015-03-09T13:00:35Z
       
  • Preface
    • Abstract: Publication date: 20 March 2015
      Source:Carbohydrate Research, Volume 405
      Author(s): Xuefei Huang , Joseph J. Barchi Jr.



      PubDate: 2015-03-09T13:00:35Z
       
  • Advances in multifunctional glycosylated nanomaterials: preparation and
           applications in glycoscience
    • Abstract: Publication date: 20 March 2015
      Source:Carbohydrate Research, Volume 405
      Author(s): Avijit K. Adak , Ben-Yuan Li , Chun-Cheng Lin
      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.
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      PubDate: 2015-03-09T13:00:35Z
       
  • Multivalent glycocyclopeptides: toward nano-sized glycostructures
    • Abstract: Publication date: 20 March 2015
      Source:Carbohydrate Research, Volume 405
      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.
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      PubDate: 2015-03-09T13:00:35Z
       
  • Polysaccharide-based nanocomposites and their applications
    • Abstract: Publication date: 20 March 2015
      Source:Carbohydrate Research, Volume 405
      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.
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      PubDate: 2015-03-09T13:00:35Z
       
  • Carbohydrate conjugation through microwave-assisted functionalization of
           single-walled carbon nanotubes using perfluorophenyl azides
    • Abstract: Publication date: 20 March 2015
      Source:Carbohydrate Research, Volume 405
      Author(s): Na Kong , Manishkumar R. Shimpi , Olof Ramström , Mingdi Yan
      Carbohydrate–functionalized single-walled carbon nanotubes (SWNTs) were synthesized using microwave-assisted reaction of perfluorophenyl azide with the nanotubes. The results showed that microwave radiation provides a rapid and effective means to covalently attach carbohydrates to SWNTs, producing carbohydrate–SWNT conjugates for biorecognition. The carbohydrate–functionalized SWNTs were furthermore shown to interact specifically with cognate carbohydrate-specific proteins (lectins), resulting in predicted recognition patterns. The carbohydrate-presenting SWNTs constitute a new platform for sensitive protein- or cell recognition, which pave the way for glycoconjugated carbon nanomaterials in biorecognition applications.
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      PubDate: 2015-03-09T13:00:35Z
       
  • Galactose grafting on poly(ε-caprolactone) substrates for tissue
           engineering: a preliminary study
    • Abstract: Publication date: 20 March 2015
      Source:Carbohydrate Research, Volume 405
      Author(s): Laura Russo , Teresa Russo , Chiara Battocchio , Francesca Taraballi , Antonio Gloria , Ugo D’Amora , Roberto De Santis , Giovanni Polzonetti , Francesco Nicotra , Luigi Ambrosio , Laura Cipolla
      The grafting of galactose units onto poly(ε-caprolactone) (PCL) substrates by a wet chemistry two-step procedure is proposed. Even though a reduction of hardness from 0.58–0.31GPa to 0.12–0.05GPa is achieved, the chemical functionalization does not negatively affect the tensile modulus (332.2±31.3MPa and 328.5±34.7MPa for unmodified and surface-modified PCL, respectively) and strength (15.1±1.3MPa and 14.8±1.5MPa as assessed before and after the surface modification, respectively), as well as the mechanical behaviour evaluated through small punch test. XPS and enzyme-linked lectin assay (ELLA) demonstrate the presence, and also the correct exposition of the saccharidic epitope on PCL substrates. The introduction of carbohydrate moieties on the PCL surfaces clearly enhances the hydrophilicity of the substrate, as the water contact angle decreases from 82.1±5.8° to 62.1±4.2°. Furthermore, preliminary biological analysis shows human mesenchymal stem cell viability over time and an improvement of cell adhesion and spreading.
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      PubDate: 2015-03-09T13:00:35Z
       
  • Synthesis and characterisation of glucose-functional glycopolymers and
           gold nanoparticles: study of their potential interactions with ovine red
           blood cells
    • Abstract: Publication date: 20 March 2015
      Source:Carbohydrate Research, Volume 405
      Author(s): Laura E. Wilkins , Daniel J. Phillips , Robert C. Deller , Gemma-Louise Davies , Matthew I. Gibson
      Carbohydrate–protein interactions can assist with the targeting of polymer- and nano-delivery systems. However, some potential protein targets are not specific to a single cell type, resulting in reductions in their efficacy due to undesirable non-specific cellular interactions. The glucose transporter 1 (GLUT-1) is expressed to different extents on most cells in the vasculature, including human red blood cells and on cancerous tissue. Glycosylated nanomaterials bearing glucose (or related) carbohydrates, therefore, could potentially undergo unwanted interactions with these transporters, which may compromise the nanomaterial function or lead to cell agglutination, for example. Here, RAFT polymerisation is employed to obtain well-defined glucose-functional glycopolymers as well as glycosylated gold nanoparticles. Agglutination and binding assays did not reveal any significant binding to ovine red blood cells, nor any haemolysis. These data suggest that gluco-functional nanomaterials are compatible with blood, and their lack of undesirable interactions highlights their potential for delivery and imaging applications.
      Graphical abstract image

      PubDate: 2015-03-09T13:00:35Z
       
  • Electrochemical synthesis of nanostructured gold film for the study of
           carbohydrate–lectin interactions using localized surface plasmon
           resonance spectroscopy
    • Abstract: Publication date: 20 March 2015
      Source:Carbohydrate Research, Volume 405
      Author(s): Jay K. Bhattarai , Abeera Sharma , Kohki Fujikawa , Alexei V. Demchenko , Keith J. Stine
      Localized surface plasmon resonance (LSPR) spectroscopy is a label-free chemical and biological molecular sensing technique whose sensitivity depends upon development of nanostructured transducers. Herein, we report an electrodeposition method for fabricating nanostructured gold films (NGFs) that can be used as transducers in LSPR spectroscopy. The NGF was prepared by electrodepositing gold from potassium dicyanoaurate solution onto a flat gold surface using two sequential controlled potential steps. Imaging by scanning electron microscopy reveals a morphology consisting of randomly configured block-like nanostructures. The bulk refractive index sensitivity of the prepared NGF is 100±2nmRIU−1 and the initial peak in the reflectance spectrum is at 518±1nm under N2(g). The figure of merit is 1.7. In addition, we have studied the interaction between carbohydrate (mannose) and lectin (Concanavalin A) on the NGF surface using LSPR spectroscopy by measuring the interaction of 8-mercaptooctyl-α-d-mannopyranoside (αMan-C8-SH) with Concanavalin A by first immobilizing αMan-C8-SH in mixed SAMs with 3,6-dioxa-8-mercaptooctanol (TEG-SH) on the NGF surface. The interaction of Con A with the mixed SAMs is confirmed using electrochemical impedance spectroscopy. Finally, the NGF surface was regenerated to its original sensitivity by removing the SAM and the bound biomolecules. The results from these experiments contribute toward the development of inexpensive LSPR based sensors that could be useful for studying glycan–protein interactions and other bioanalytical purposes.
      Graphical abstract image

      PubDate: 2015-03-09T13:00:35Z
       
  • Fluorous-based carbohydrate Quartz Crystal Microbalance
    • Abstract: Publication date: 20 March 2015
      Source:Carbohydrate Research, Volume 405
      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–carbohydrate interaction have been detected afterward.
      Graphical abstract image

      PubDate: 2015-03-09T13:00:35Z
       
  • Hyaluronic acid-modified multiwalled carbon nanotubes for targeted
           delivery of doxorubicin into cancer cells
    • Abstract: Publication date: 20 March 2015
      Source:Carbohydrate Research, Volume 405
      Author(s): Xueyan Cao , Lei Tao , Shihui Wen , Wenxiu Hou , Xiangyang Shi
      Development of novel drug carriers for targeted cancer therapy with high efficiency and specificity is of paramount importance and has been one of the major topics in current nanomedicine. Here we report a general approach to using multifunctional multiwalled carbon nanotubes (MWCNTs) as a platform to encapsulate an anticancer drug doxorubicin (DOX) for targeted cancer therapy. In this approach, polyethyleneimine (PEI)-modified MWCNTs were covalently conjugated with fluorescein isothiocyanate (FI) and hyaluronic acid (HA). The formed MWCNT/PEI–FI–HA conjugates were characterized via different techniques and were used as a new carrier system to encapsulate the anticancer drug doxorubicin for targeted delivery to cancer cells overexpressing CD44 receptors. We show that the formed MWCNT/PEI–FI–HA/DOX complexes with a drug loading percentage of 72% are water soluble and stable. In vitro release studies show that the drug release rate under an acidic condition (pH 5.8, tumor cell microenvironment) is higher than that under physiological condition (pH 7.4). Cell viability assay demonstrates that the carrier material has good biocompatibility in the tested concentration range, and the MWCNT/PEI–FI–HA/DOX complexes can specifically target cancer cells overexpressing CD44 receptors and exert growth inhibition effect to the cancer cells. The developed HA-modified MWCNTs hold a great promise to be used as an efficient anticancer drug carrier for tumor-targeted chemotherapy.
      Graphical abstract image

      PubDate: 2015-03-09T13:00:35Z
       
  • Synthesis and evaluation of glyco-coated liposomes as drug carriers for
           active targeting in drug delivery systems
    • Abstract: Publication date: 20 March 2015
      Source:Carbohydrate Research, Volume 405
      Author(s): Akiharu Ueki , Keita Un , Yuka Mino , Mitsuru Yoshida , Shigeru Kawakami , Hiromune Ando , Hideharu Ishida , Fumiyoshi Yamashita , Mitsuru Hashida , Makoto Kiso
      Novel sugar-conjugated cholesterols, β-Gal-, α-Man-, β-Man-, α-Fuc-, and β-Man-6P-S-β-Ala-Chol, were synthesized and incorporated into liposomes. In vitro experiments using the glyco-coated liposomes showed that the glyco-coated liposomes are efficiently taken up by cells expressing carbohydrate-binding receptors selectively. Glyco-coated liposomes are promising candidates for drug delivery vehicles.
      Graphical abstract image

      PubDate: 2015-03-09T13:00:35Z
       
  • Sublingual injection of microparticles containing glycolipid ligands for
           NKT cells and subunit vaccines induces antibody responses in oral cavity
    • Abstract: Publication date: 20 March 2015
      Source:Carbohydrate Research, Volume 405
      Author(s): Elizabeth S. DeLyria , Dapeng Zhou , Jun Soo Lee , Shailbala Singh , Wei Song , Fenge Li , Qing Sun , Hongzhou Lu , Jinhui Wu , Qian Qiao , Yiqiao Hu , Guodong Zhang , Chun Li , K. Jagannadha Sastry , Haifa Shen
      Natural Killer T (NKT) cells are a unique type of innate immune cells which exert paradoxical roles in animal models through producing either Th1 or Th2 cytokines and activating dendritic cells. Alpha-galactosylceramide (αGalCer), a synthetic antigen for NKT cells, was found to be safe and immune stimulatory in cancer and hepatitis patients. We recently developed microparticle-formulated αGalCer, which is selectively presented by dendritic cells and macrophages, but not B cells, and thus can avoid the anergy of NKT cells. In this study, we have examined the immunogenicity of microparticles containing αGalCer and protein vaccine components through sublingual injection in mice. The results showed that sublingual injection of microparticles containing αGalCer and ovalbumin triggered IgG responses in serum (titer >1:100,000), which persisted for more than 3months. Microparticles containing ovalbumin alone also induced comparable level of IgG responses. However, immunoglobulin subclass analysis showed that sublingually injected microparticles containing αGalCer and ovalbumin induced 20 fold higher Th1 biased antibody (IgG2c) than microparticles containing OVA alone (1:20,000 as compared to 1:1000 titer). Sublingual injection of microparticles containing αGalCer and ovalbumin induced secretion of both IgG (titer >1:1000) and IgA (titer=1:80) in saliva secretion, while microparticles containing ovalbumin alone only induced secretion of IgG in saliva. Our results suggest that sublingual injection of microparticles and their subsequent trafficking to draining lymph nodes may induce adaptive immune responses in mucosal compartments. Ongoing studies are focused on the mechanism of antigen presentation and lymphocyte biology in the oral cavity, as well as the toxicity and efficacy of these candidate microparticles for future applications.
      Graphical abstract image

      PubDate: 2015-03-09T13:00:35Z
       
  • Synthesis and cell-selective antitumor properties of amino acid conjugated
           tumor-associated carbohydrate antigen-coated gold nanoparticles
    • Abstract: Publication date: 20 March 2015
      Source:Carbohydrate Research, Volume 405
      Author(s): Souvik Biswas , Scott H. Medina , Joseph J. Barchi Jr.
      The Thomsen Friedenreich antigen (TFag) disaccharide is a tumor-associated carbohydrate antigen (TACA) found primarily on carcinoma cells and rarely expressed in normal tissue. The TFag has been shown to interact with Galectin-3 (Gal-3), one in a family of β-galactoside binding proteins. Galectins have a variety of cellular functions, and Gal-3 has been shown to be the sole galectin with anti-apoptotic activity. We have previously prepared gold nanoparticles (AuNP) coated with the TFag in various presentations as potential anti-adhesive therapeutic tools or antitumor vaccine platforms. Here we describe the synthesis of TFag–glycoamino acid conjugates attached to gold nanoparticles through a combined alkane/PEG linker, where the TFag was attached to either a serine or threonine amino acid. Particles were fully characterized by a host of biophysical techniques, and along with a control particle carrying hydroxyl-terminated linker units, were evaluated in both Gal-3 positive and negative cell lines. We show that the particles bearing the saccharides selectively inhibited tumor cell growth of the Gal-3 positive cells significantly more than the Gal-3 negative cells. In addition, the threonine-attached TF particles were more potent than the serine-attached constructs. These results support the use of AuNP as antitumor therapeutic platforms, targeted against cell lines that express specific lectins that interact with TFag.
      Graphical abstract image

      PubDate: 2015-03-09T13:00:35Z
       
  • A linear synthesis of gemcitabine
    • Abstract: Publication date: 10 April 2015
      Source:Carbohydrate Research, Volume 406
      Author(s): Kylie Brown , Alex Weymouth-Wilson , Bruno Linclau
      Gemcitabine, 2′-deoxy-2′,2′-difluorocytidine, is currently prescribed against a number of cancers. Here we report a linear synthesis of gemcitabine with a high-yielding direct conversion of 3,5-di-O-benzoyl-2-deoxy-2,2-difluororibose into the corresponding glycosyl urea as the key step, followed by conventional conversion to the cytosine base via the uracil derivative. The process proceeded with modest anomeric selectivity.
      Graphical abstract image

      PubDate: 2015-02-13T06:44:34Z
       
 
 
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