Carbohydrate research

Publisher: ScienceDirect (Online service), Elsevier

Journal description

Current impact factor: 2.03

Impact Factor Rankings

Additional details

5-year impact 2.17
Cited half-life 0.00
Immediacy index 0.45
Eigenfactor 0.02
Article influence 0.53
Other titles Carbon (En ligne)
ISSN 1873-426X
OCLC 300759987
Material type Periodical, Internet resource
Document type Internet Resource, Journal / Magazine / Newspaper

Publisher details

Elsevier

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    • Publisher last contacted on 18/10/2013
  • Classification
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Publications in this journal

  • [Show abstract] [Hide abstract]
    ABSTRACT: Chemotaxis is one of the most essential cell physiological responses, which was developed in parallel the molecular evolution of signal molecules. Previously good correlations were found between chemotactic moieties and physicochemical properties (SEA, solubility, pKa) of peptide type ligands in Tetrahymena model. However, references are rather weak in eukaryotic chemotaxis about significance of simple carbohydrates. In the present work our goal is (i) to investigate the chemotactic effect of 10 mono- and disaccharides in the eukaryotic Tetrahymena pyriformis; (ii) to describe effective ligands with physicochemical parameters; (iii) to test whether sugars are acting via induction of metabolic pathways. Our results are: (i) the tested sugars can trigger both significant attractant (d-glucose, d-mannose) and significant repellent (d-glucosamine, d-fructose, N-acetyl-d-galactosamine, d-arabinose) effects, while some of the sugars (maltose, lactose, sucrose, d-galactose) had no effect. (ii) Correlations were described between the chemotactic effectiveness of the ligands and their physicochemical characters (TPSA, XLogP), which are supposed to influence the internalization of the sugars. (iii) All ligands proved to have low selection potential, which refers to a 'short-term' receptor moiety or influencing specific metabolic pathways. (iv) Starvation elicited modified, strong chemoattractive responsiveness towards glucose; however, it was independent of concentration while 1 h insulin treatment resulted in an increased and concentration dependent chemotaxis induced by glucose. Copyright © 2015 Elsevier Ltd. All rights reserved.
    Carbohydrate research 04/2015; 407. DOI:10.1016/j.carres.2015.02.009
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    ABSTRACT: 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. Copyright © 2015 Elsevier Ltd. All rights reserved.
    Carbohydrate research 02/2015; in press. DOI:10.1016/j.carres.2015.01.014
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    ABSTRACT: 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. Copyright © 2015 Elsevier Ltd. All rights reserved.
    Carbohydrate research 02/2015; 407. DOI:10.1016/j.carres.2015.01.022
  • Carbohydrate research 05/2014;
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    ABSTRACT: The leaves of the annual plant Impatiens parviflora DC., a herbal medicine in Asian countries and invasive in managed forests and natural environments in Central Europe, have the potential as a source of bioactive phenolic compounds and polysaccharides. Extractives accounted for ∼22% of the leaves, whereby, the methanolic extract contains mainly caffeic acid, ferulic acid, kaempferol, and quercetin derivatives, and 1,2,4-trihydroxynaphthalene-1-O-glucoside. From the pre-extracted leaves, non-cellulosic polysaccharides were isolated by a five-step extraction procedure using as extractants cold water, 0.05M EDTA and DMSO in the first three steps, and 1% and 5% NaOH in the last two steps. The isolated polysaccharide fractions were characterized by chemical, physicochemical and spectroscopic analyses (FTIR and 1H NMR). The first three fractions contained mainly pectin and the alkali-extracted ones methylglucuronoxylan and arabinogalactan. The suggested structural features were confirmed using HSQC NMR and COSY experiments for polysaccharides of the EDTA-fraction and the Pronase-treated 5% NaOH-fraction. The EDTA fraction comprised a pectin with low degree of methyl-esterification (DM, 37%) with few rhamnogalacturonan RG I segments bearing β-1,4-galactan as side chains. The alkali-extracted fraction comprised a degraded methylglucuronoxylan and type II 3,6-arabinogalactan in about equal amounts.
    Carbohydrate research 05/2014; DOI:10.1016/j.carres.2014.01.016
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    ABSTRACT: A small set of N-bridged 1-deoxynojirimycin dimers has been synthesized and evaluated as potential inhibitors of insect trehalase from midge larvae of C. riparius, porcine trehalase as the mammalian counterpart and α-amylase from human saliva. All the tested compounds (2-4) proved to be active (micromolar range activity) against insect trehalase, showing selectivity towards the insect glycosidase. No activity was observed against α-amylase.
    Carbohydrate research 05/2014; DOI:10.1016/j.carres.2013.12.025
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    ABSTRACT: Human heparanase is a heparan sulfate degrading enzyme located in the extracellular matrix playing a decisive role in angiogenesis and tumour metastasis. Translated as a 65kDa inactive prae-form, the protein is processed into an 8kDa and a 50kDa subunit which form a non-covalently associated active heterodimer. We have expressed the two subunits separately in E.coli which yielded active human heparanase upon reconstitution. The two purified subunits folded independently and secondary structure analysis by far-UV CD spectroscopy gave 33.1/11.1% α/ß content for the 50kDa subunit and 6.9/49% α/ß content for the 8kDa subunit. This heparanase expression system is easy and can be used for efficient screening for enzyme inhibitors.
    Carbohydrate research 05/2014; DOI:10.1016/j.carres.2014.01.002
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    ABSTRACT: A set of new metabolically stable arabinose 5-phosphate analogues possessing phosphate mimetic groups at position 5 was synthesised. Their ability to interact with arabinose 5-phosphate isomerase from Pseudomonas aeruginosa was evaluated by STD-NMR studies. The synthesised compounds were also characterised for their activity in vivo on P. aeruginosa and E. coli strains. Unfortunately, none of the synthesised compounds was able neither to bind API nor to inhibit bacterial growth.
    Carbohydrate research 05/2014; DOI:10.1016/j.carres.2014.01.004
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    ABSTRACT: The synthesis of nine new, bifunctional organocatalysts having carbohydrate scaffolds has been accomplished. In these catalysts both of the catalytic amino and thiourea functions are directly attached to a carbohydrate core. The activities of the newly prepared catalysts were tested in a Michael addition.
    Carbohydrate research 05/2014; DOI:10.1016/j.carres.2013.12.026
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    ABSTRACT: Complementarity in lectin-glycan interactions in situ is assumed to involve spatial features in both the lectin and the glycan, giving a functional meaning to structural aspects of the lectin beyond its carbohydrate-binding site. In combining protein engineering with glycocluster synthesis, it is shown that the natural linker length of a tandem-repeat-type human lectin (galectin-4) determines binding properties in two binding assays (using surface-presented glycoprotein and cell surface assays). The types of glycocluster tested included bivalent lactosides based on tertiary amides of terephthalic, isophthalic, 2,6-naphthalic and oxalic acids as well as bivalent H(type 2) trisaccharides grafted on secondary/tertiary terephthalamides and two triazole-linker-containing cores. The presented data reveal a marked change in susceptibility to the test compounds when turning the tandem-repeat-type to a proto-type-like display. The testing of glycoclusters is suggested as a general strategy to help to delineate the significance of the distinct structural features of lectins beyond their contact sites to the glycan.
    Carbohydrate research 05/2014; DOI:10.1016/j.carres.2013.12.024
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    ABSTRACT: Different rhamnose-rich polysaccharides (RRP) were identified in the cell envelope of the Gram-positive bovine mastitis isolate Streptococcus dysgalactiae 2023. Structural investigations of the 1D and 2D nuclear magnetic resonance experiments as well as chemical analyses identified as main components l-Rha and d-GalNAc. Two main RRP were characterized, namely 1 being composed of the repeating unit {→3)-α-l-Rhap-(1→2)-[α-d-GalpNAc-(1→3)-β-d-GalpNAc-(1→3)-]α-l-Rhap-(1} and 2 possessing the repeat [→2)-α-l-Rhap-(1→3)-α-l-Rhap-(1→].
    Carbohydrate research 05/2014; DOI:10.1016/j.carres.2013.12.018
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    ABSTRACT: Chitosan oligosaccharides have diverse biological activities with potentially valuable applications, for example, in the fields of medicine and agriculture. These functionalities are thought to depend on their degree of polymerization and acetylation, and possibly on specific patterns of acetylation. Chitosan oligomers with fully defined architecture are difficult to produce, and their complete analysis is demanding. Analysis is typically done using MS or NMR, requiring access to expensive infrastructure, and yielding unequivocal results only in the case of rather small oligomers. We here describe a simple and cost-efficient method for the sequencing of μg amounts of chitosan oligosaccharides which is based on the sequential action of two recombinant glycosidases, namely an exo-β-N-acetylhexosaminidase (GlcNAcase) from Bacillus subtilis 168 and an exo-β-d-glucosaminidase (GlcNase) from Thermococcus kodakarensis KOD1. Starting from the non-reducing end, GlcNAcase and GlcNase specifically remove N-acetyl glucosamine (A) and glucosamine (D) units, respectively. By the sequential addition and removal of these enzymes in an alternating way followed by analysis of the products using high-performance thin-layer chromatography, the sequence of chitosan oligosaccharides can be revealed. Importantly, both enzymes work under identical conditions so that no buffer exchange is required between steps, and the enzyme can be removed conveniently using simple ultra-filtration devices. As proof-of-principle, the method was used to sequence the product of enzymatic deacetylation of chitin pentamer using a recombinant chitin deacetylase from Vibrio cholerae which specifically removes the acetyl group from the second unit next to the non-reducing end of the substrate, yielding mono-deacetylated pentamer with the sequence ADAAA.
    Carbohydrate research 04/2014; 392C:16-20. DOI:10.1016/j.carres.2014.04.006
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    ABSTRACT: Capsular polysaccharide was isolated by the phenol-water extraction of Acinetobacter baumannii ACICU cells and studied by sugar analysis, partial acid hydrolysis, and 1D and 2D (1)H and (13)C NMR spectroscopy. The polysaccharide was found to contain 5,7-diacetamido-3,5,7,9-tetradeoxy-l-glycero-l-manno-non-2-ulosonic or di-N-acetylpseudaminic acid (Pse5Ac7Ac), and the following structure of the branched tetrasaccharide repeating unit was established: The genes present in the polysaccharide gene cluster of A. baumannii ACICU are appropriate to the structure established.
    Carbohydrate research 04/2014; 391C:89-92. DOI:10.1016/j.carres.2014.04.002
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    ABSTRACT: The first total synthesis of p-methoxyphenyl α-l-fucopyranosyl-(1→6)-α-d-galactopyranosyl-(1→4)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside (2) was achieved starting from five monosaccharide building blocks. This structure represents the repeating unit of the polysaccharide isolated from edible mushroom Calocybe indica var. APK2, and was synthesized in high overall yield via a convergent '3+2' glycosylation strategy.
    Carbohydrate research 04/2014; 391C:43-47. DOI:10.1016/j.carres.2014.04.004
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    ABSTRACT: Mono[6-deoxy-6-(pentacosa-10,12-diynyl amidomethyl)]-β-cyclodextrin was successfully synthesized by reacting mono-6-amino-6-deoxy-β-cyclodextrin with N-hydroxysuccinimide ester of 10,12-pentacosadiynoic acid in DMF. The modified β-cyclodextrin self-assembled and aggregated to form a worm-like supramolecular structure, and the novel supramolecular aggregates were studied using 2D nuclear magnetic resonance spectroscopy, X-ray powder diffraction, thermogravimetry, and electron microscopy. Interestingly, the synthesized pentacosa-10,12-diynyl amidomethyl-β-cyclodextrin formed columnar type self-aggregates and it was clearly differentiated from cage-like structure of native β-cyclodextrin.
    Carbohydrate research 04/2014; 391C:37-42. DOI:10.1016/j.carres.2014.03.022
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    ABSTRACT: Gemcitabine is a fluorinated nucleoside currently administered against a number of cancers. It consists of a cytosine base and a 2-deoxy-2,2-difluororibose sugar. The synthetic challenges associated with the introduction of the fluorine atoms, as well as with nucleobase introduction of 2,2-difluorinated sugars, combined with the requirement to have an efficient process suitable for large scale synthesis, have spurred significant activity towards the synthesis of gemcitabine exploring a wide variety of synthetic approaches. In addition, many methods have been developed for selective crystallisation of diastereomeric (including anomeric) mixtures. In that regard, the 2-deoxy-2,2-difluororibose sugar is one of the most investigated fluorinated carbohydrates in terms of its synthesis. The versatility of synthetic methods employed is illustrative of the current state of the art of fluorination methodology for the synthesis of CF2-containing carbohydrates, and involves the use of fluorinated building blocks, as well as nucleophilic and electrophilic fluorination of sugar precursors.
    Carbohydrate research 03/2014; 387C:59-73. DOI:10.1016/j.carres.2014.01.024
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    ABSTRACT: Heptakis{6-(4-hydroxymethyl-1H-[1,2,3]triazol-1-yl)-6-deoxy}-β-cyclodextrin (HTβCD) and heptakis{6-(4-sulfonylmethyl-1H-[1,2,3]triazol-1-yl)-6-deoxy}-β-cyclodextrin (STβCD) were prepared using copper(I)-catalyzed azide-alkyne cycloaddition between 6-azido-6-deoxy-β-CD and one of two alkynes, propargyl alcohol, and sodium propargyl sulfonate, respectively. The structures of HTβCD and STβCD were characterized by NMR techniques. NMR interpretations and computer modeling suggested that the limited freedom of rotation of the triazole moieties keeps HTβCD and STβCD rigid and compact. Water solubility tests of HTβCD and STβCD showed that the minimum water solubility of HTβCD and STβCD is at least 20times higher than that of β-CD. MTT assay showed that HTβCD and STβCD did not influence the cell viability under 1mM. A phase-solubility study of prednisolone with the CD derivatives showed increased solubility of prednisolone in the presence of increasing concentrations of HTβCD and STβCD.
    Carbohydrate research 03/2014; 391C:22-28. DOI:10.1016/j.carres.2014.03.020