Carbohydrate research

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Publications in this journal

  • Carbohydrate research 05/2014;
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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;
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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;
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    ABSTRACT: Mannosylerythritol lipids (MELs) are mainly produced by strains of the genus Pseudozyma and by Ustilago maydis. These glycolipid biosurfactants exhibit not only excellent surface-active properties but also versatile bioactivities. Mannosylerythritol lipid-A (MEL-A) is worth investigating due to its self-assembling property. In this work, crude MELs were produced by resting Pseudozyma aphidis ZJUDM34 cells using different culture media. MEL-A fractions were isolated and identified using high-performance liquid chromatography combined with mass spectrometry (HPLC-MS) and gas chromatography combined with mass spectrometry (GC-MS). The results showed that MEL-A homologs had long unsaturated fatty acid chains, and the chain lengths range from C8 to C20. Nuclear magnetic resonance (NMR) was employed to confirm the chemical structures of the MEL-A homologs. Fermentation medium without NaNO3 and medium with manganese ions enhanced MEL-A production by Pseudozyma aphidis ZJUDM34.
    Carbohydrate research 04/2014; 392C:1-6.
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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.
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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.
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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.
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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.
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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.
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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.
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    ABSTRACT: A β-glucan called schizophyllan (SPG) forms a stoichiometric complex with polynucleotides with its two main chain glucoses interacting with one nucleotide base. This complex can be used as a Dectin-1 targeting delivery for therapeutic oligonucleotides (ODN), where Dectin-1 is a membrane receptor of immunocyte cell that can recognize β-glucans. Our in vivo and in vitro assays phenomenologically implied that such a targeting is indeed achieved. However, we do not know whether SPG/ODN complexes are recognized by Dectin-1. In this study, we examined the binding affinity between SPG/poly(dA) complex and a constructed protein representing the extracellular carbohydrate-recognition domain of murine Dectin-1 by use of quartz-crystal microbalance (QCM). It was shown that the SPG/dA60 complex made form phosphodiester was recognized in the same manner as SPG, while its dissociation constant (Kd) was much larger than SPG itself, that is, less affinity than SPG. When the phosphodiester linkage of dA60 was changed to phosphorothioate (denoted by dA60(S)), the QCM frequency decrease was dramatically enhanced. There seemed to be multiple binding sites; the same site as SPG and SPG/dA60, and an additional site (or sites) for which phosphate anion specific electrostatic interactions were mainly involved. Interestingly, this new site showed a comparable affinity with that between SPG and its original binding site.
    Carbohydrate research 03/2014; 391C:1-8.
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    ABSTRACT: 2'-Deoxyzebularine and its α-anomer have been efficiently synthesized with relatively high stereoselectivity by a modified procedure of the silyl method of the N-glycosidic bond formation. An SnCl4-catalyzed condensation of silylated pyrimidin-2-one with 1-α-chloro-3,5-di-O-p-toluoyl-2-deoxy-d-ribofuranose under kinetic control condition (-33°C, 1,2-dichloroethane) led to the mixture of β- and α-anomeric nucleosides in 3:1 ratio. Analogous condensation at +35°C (thermodynamic control conditions) provided mainly p-toluoyl protected α-2'-deoxyzebularine (α:β=4:1), easily separated by crystallization from the anomeric mixture. The structures of both 2'-deoxyzebularine anomers were confirmed by X-ray analysis of the crystals and conformational studies in solution performed using an NMR method.
    Carbohydrate research 03/2014; 392C:7-15.
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    ABSTRACT: A polysaccharide with an estimated weight-average molar mass of 5.35×10(5) was obtained from an aqueous extract of pseudobulbs of Cyrtopodium andersonii R. Br. It was composed of d-glucose and d-mannose in 1:3 molar ratio. Chemical and spectroscopic analyses revealed a linear structure of the polymer with a backbone composed of (1→4)-linked β-d-glucopyranosyl and mannopyranosyl units slightly branched at C-2, C-3, and C-6 by side chains, as terminal non reducing residues of d-mannopyranose and d-glucopyranose. It was found to contain 14.6% of acetyl groups substituted at C-2 of (1→4)-linked β-d-mannopyranosyl units. The acetylated glucomannan demonstrated antiinflammatory and antiulcerogenic activities.
    Carbohydrate research 03/2014; 391C:16-21.
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    ABSTRACT: The present article shows the objective figures of the contributions of South American research centers to Carbohydrate Research during its 50years of history, measured in terms of members of the Editorial Board, number of articles and citations to them, together with a country-based comparison, and the progression of these contributions with time. In addition, it also shows the subjective feelings of the author toward the same journal.
    Carbohydrate research 03/2014; 390C:71-75.
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    ABSTRACT: A computational study was conducted to gain insight into the pyrolytic deformylations of levoglucosenone and isolevoglucosenone. Present B3LYP/6-31G(∗) and CBS-QB3 calculations provide valuable evidence to rule out the formation of isolevoglucosenone during the pyrolytic degradation of cellulosic materials. This, along with the supplementary data herein presented and with other recent reports, suggest that levoglucosenone should not be formed directly from levoglucosan (as proposed in numerous reports), but rather from another intermediate, such as 1,4:3,6-dianhydro-α-d-glucopyranose.
    Carbohydrate research 03/2014; 390C:76-80.
  • Carbohydrate research 03/2014;
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    ABSTRACT: A fast liquid chromatography method for separation and determination of myo-inositol is reported. Determination of the biologically important isomer of inositols, myo-inositol, was optimized to avoid overlapping to possible interferents according to European Pharmacopoeia (glycerol, d-mannitol) and saccharose. The method in HILIC mode is extremely selective to other carbohydrates which allows to separate myo-inositol from allo- and d-chiro-inositol with resolution 12.3 and 5.2, resp. and this way it enables to separate myo-inostiol from contingent carbohydrates present in a sample matrix. Retention time of myo-inositol was 12min at 10°C, though higher temperatures (25°C or 40°C) or higher water content in the mobile phase could speed up the separation and determination to four minutes. LOD of the method was 9mg/L at 10°C, and 5mg/L at 25°C, resp.
    Carbohydrate research 03/2014; 391C:55-60.
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    ABSTRACT: The synthesis of the three 6″-deoxy-6″-thio glycolipid analogues β-d-Gal-(1→6)-β-d-Gal-(1→4)-β-d-Glu-(1→OCH2)-[1,2,3]-triazole-1-dodecane, β-d-Gal-(1→4)-β-d-Glu-(1→4)-β-d-Glu-(1→OCH2)-[1,2,3]-triazole-1-dodecane and β-d-Gal-(1→4)-β-d-Glu-(1→4)-β-d-Glu-(1→OCH2)-[1,2,3]-triazole-1-octadecane is presented. Glycosylation at position O-4' of a propargyl cellobioside glycosyl acceptor and position O-6' of a propargyl lactoside glycosyl acceptor with a 6-deoxy-6-thio galactosyl donor gave rise to two unique trisaccharides that in turn underwent copper-catalyzed azide-alkyne cycloadditions with either 1-azidododecane or 1-azidooctadecane. The potential for each of these analogues to function as tethers of lipid bilayers to Au(111) surface was assessed by differential capacitance experiments. A monolayer of the previously described monosaccharide 1-octadecane-4-(6-thio-β-d-galacto-pyranosyloxymethyl)-[1,2,3]-triazole either self-assembled or prepared by Langmuir-Blodgett (LB) transfer was found to support an outer leaflet monolayer (DMPC/cholesterol, 70:30) deposited by Langmuir-Schaefer (LS) touch. The bilayers obtained with this monosaccharide analogue had minimum differential capacitances of 1.0 and 0.9μF/cm(2) when the inner monolayer was prepared by self-assembly and LS touch, respectively. Attempts to produce bilayers using the trisaccharides synthesized here were unsuccessful; we are attributing these unsuccessful results mostly to the high water solubility of trisaccharides combined with the relatively short length of the hydrocarbon chains used in this study.
    Carbohydrate research 03/2014; 390C:50-58.