Carbohydrate Research
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Synthesis of N-substituted iminosugars from 2'-carbonyl-C-glycofuranosides.
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Under basic conditions 2'-carbonyl 5-N-substituted-C-glycofuranosides undergo a tandem beta-elimination and intramolecular hetero-Michael addition to form N-substituted iminosugar derivatives in good to excellent yields.
PMID: 19917320 [PubMed - in process] (Source: Carbohydrate Research)
Source: Carbohydrate Research - November 19, 2009 Category: Genetics & Stem Cells Authors: Luo H, Zou W, Shao H Tags: Carbohydr Res Source Type: journals
Gene cloning and catalysis features of a new mannitol-1-phosphate dehydrogenase (BbMPD) from Beauveria bassiana.
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A long-chain mannitol-1-phosphate dehydrogenase (MPD) was characterized for the first time from fungal entomopathogen Beauveria bassiana by gene cloning, heterogeneous expression and activity analysis. The cloned gene BbMPD consisted of a 1334-bp open reading frame (ORF) with a 158-bp intron and the 935-bp upstream and 780-bp downstream regions. The ORF-encoded 391-aa protein (42kDa) showed less than 75% sequence identity to 17 fungal MPDs documented and shared two conserved domains with the fungal MPD family at the N- and C-terminus, respectively. The new enzyme was expressed well in the Luria-Bertani culture of engin...
Source: Carbohydrate Research - November 4, 2009 Category: Genetics & Stem Cells Authors: Wang ZL, Ying SH, Feng MG Tags: Carbohydr Res Source Type: journals
Conversion of Japanese red pine wood (Pinus densiflora) into valuable chemicals under subcritical water conditions.
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A comparative study on the decomposition of Japanese red pine wood under subcritical water conditions in the presence and absence of phosphate buffer was investigated in a batch-type reaction vessel. Since cellulose makes up more than 40-45% of the components found in most wood species, a series of experiments were also carried out using pure cellulose as a model for woody biomass. Several parameters such as temperature and residence time, as well as pH effects, were investigated in detail. The best temperature for decomposition and hydrolysis of pure cellulose was found around 270 degrees C. The effects of the initial...
Source: Carbohydrate Research - November 3, 2009 Category: Genetics & Stem Cells Authors: Asghari FS, Yoshida H Tags: Carbohydr Res Source Type: journals
NMR studies of the conformation of the natural sweetener rebaudioside A.
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Rebaudioside A is a natural sweetener from Stevia rebaudiana in which four beta-d-glucopyranose units are attached to the aglycone steviol. Its (1)H and (13)C NMR spectra in pyridine-d(5) were assigned using 1D and 2D methods. Constrained molecular dynamics of solvated rebaudioside using NMR constraints derived from ROESY cross peaks yielded the orientation of the beta-d-glucopyranose units. Hydrogen bonding was examined using the temperature coefficients of the hydroxyl chemical shifts, ROESY and long-range COSY spectra, and proton-proton coupling constants.
PMID: 19889398 [PubMed - as supplied by publisher] (Sour...
Source: Carbohydrate Research - November 2, 2009 Category: Genetics & Stem Cells Authors: Steinmetz WE, Lin A Tags: Carbohydr Res Source Type: journals
Electrospinning of poly(vinyl alcohol)-water-soluble quaternized chitosan derivative blend.
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Defect free mats containing a cationic polysaccharide, chitosan derivative such as N-[(2-hydroxy-3-trimethylammonium)propyl] chitosan chloride (HTCC), have been prepared using electrospinning of an aqueous solution of poly(vinyl alcohol) (PVA)-HTCC blends. HTCC, a water-soluble derivative of chitosan, was synthesized via the reaction between glycidyl-trimethylammonium chloride and chitosan. Solutions of PVA-HTCC Blends were electrospun. The morphology, diameter and structure of the produced electrospun nanofibres were examined by scanning electron microscopy (SEM). The average fibre diameter was in the range of 200-600...
Source: Carbohydrate Research - October 31, 2009 Category: Genetics & Stem Cells Authors: Alipour SM, Nouri M, Mokhtari J, Bahrami SH Tags: Carbohydr Res Source Type: journals
Synthesis of highly ordered cellulose II in vitro using cellodextrin phosphorylase.
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Synthesis of cellulose in vitro is expected to afford tailor-made cellulosic materials with highly homogeneous structure compared to natural cellulosic materials. Here we report the enzymatic synthesis of cellulose II with high crystallinity from glucose and alpha-glucose 1-phosphate (alphaG1P) by cellodextrin phosphorylase (CDP). Although glucose had been believed not to act as a glucosyl acceptor of CDP, a significant amount of insoluble cellulose was precipitated without accumulation of soluble cello oligosaccharides when glucose was mixed with alphaG1P and CDP. This phenomenon can be explained in terms of the large...
Source: Carbohydrate Research - October 29, 2009 Category: Genetics & Stem Cells Authors: Hiraishi M, Igarashi K, Kimura S, Wada M, Kitaoka M, Samejima M Tags: Carbohydr Res Source Type: journals
Dielectric properties of two diastereoisomers of the arabinose and their equimolar mixture.
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This study reveals that both d- and l- of arabinose exhibit alpha-relaxation peaks with the same shape for the same alpha-relaxation time tau(alpha), and the same steepness index for the T(g)-scale T-dependence of tau(alpha). However, the two isomers have slightly different glass transition temperatures T(g)'s, and their secondary gamma-relaxation times also differ slightly from the previously observed gamma-relaxation in d-ribose at the same temperature. However, when samples of both investigated monosaccharides are annealed at higher temperatures, their glass transition temperatures become nearly identical. This is an ef...
Source: Carbohydrate Research - October 7, 2009 Category: Genetics & Stem Cells Authors: Kaminski K, Kaminska E, Pawlus S, Wlodarczyk P, Paluch M, Ziolo J, Kasprzycka A, Szeja W, Ngai KL, Pilch J Tags: Carbohydr Res Source Type: journals
Efficient microwave-assisted synthesis of 5-hydroxymethylfurfural from concentrated aqueous fructose.
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Studies on the HCl-catalysed microwave-assisted dehydration of highly concentrated aqueous fructose (27wt%) to 5-hydroxymethylfurfural (HMF) revealed a significant increase in the fructose conversion rate over the conventional heated systems. Water, being the most benign solvent and therefore ideal for green and sustainable chemistry, normally is a poor solvent for the dehydration process resulting in low HMF selectivities and yields. However, reaction at 200 degrees C with microwave irradiation with a short reaction time of only 1s resulted in good HMF selectivity of 63% and fructose conversion of 52%, while prolonged...
Source: Carbohydrate Research - October 1, 2009 Category: Genetics & Stem Cells Authors: Hansen TS, Woodley JM, Riisager A Tags: Carbohydr Res Source Type: journals
Presence of 1-->3-linked 2-O-beta-d-xylopyranosyl-alpha-l-arabinofuranosyl side chains in cereal arabinoxylans.
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Presence of 1-->3-linked 2-O-beta-d-xylopyranosyl-alpha-l-arabinofuranosyl side chains in cereal arabinoxylans.
Carbohydr Res. 2009 Oct 2;
Authors: Pastell H, Virkki L, Harju E, Tuomainen P, Tenkanen M
The presence of a fairly uncommon side chain 2-O-beta-d-xylopyranosyl-alpha-l-arabinofuranosyl in arabinoxylans (AX) from eight different cereal by-products was investigated, using (1)H NMR spectroscopy and high-performance anion-exchange chromatography with pulsed amperometric detection (HPAEC-PAD) after Shearzyme((R)) (GH10 endo-1,4-beta-d-xylanase) hydrolysis. This disaccharide side group was present in sig...
Source: Carbohydrate Research - October 1, 2009 Category: Genetics & Stem Cells Authors: Pastell H, Virkki L, Harju E, Tuomainen P, Tenkanen M Tags: Carbohydr Res Source Type: journals
Structural studies of the O-antigenic polysaccharides from the enteroaggregative Escherichia coli strain 94/D4 and the international type strain Escherichia coli O82.
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The structure of the O-antigen polysaccharides (PS) from the enteroaggregative Escherichia coli strain 94/D4 and the international type strain E. coli O82 have been determined. Component analysis and (1)H, (13)C, and (31)P NMR spectroscopy experiments were employed to elucidate the structure. Inter-residue correlations were determined by (1)H, (13)C-heteronuclear multiple-bond correlation, and (1)H, (1)H-NOESY experiments. d-GroA as a substituent is linked via its O-2 in a phosphodiester-linkage to O-6 of the alpha-d-Glcp residue. The PS is composed of tetrasaccharide repeating units with the following structure: -->...
Source: Carbohydrate Research - October 1, 2009 Category: Genetics & Stem Cells Authors: Vilchez S, Lundborg M, Urbina F, Weintraub A, Widmalm G Tags: Carbohydr Res Source Type: journals
Structural studies of an immunoenhancing water-soluble glucan isolated from hot water extract of an edible mushroom, Pleurotus florida, cultivar Assam Florida.
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An immunoenhancing polysaccharide isolated from the hot water extract of the fruiting bodies of an edible mushroom Pleurotus florida, cultivar Assam Florida, was found to consist of only d-glucose as a monosaccharide constituent. On the basis of total acid hydrolysis, methylation analysis, periodate oxidation, Smith degradation, and NMR experiments ((1)H, (13)C, DEPT-135, DQF-COSY, TOCSY, NOESY, ROESY, HMQC, and HMBC), the structure of the repeating unit of the polysaccharide was established as This glucan stimulates macrophages, splenocytes, and thymocytes.
PMID: 19836727 [PubMed - as supplied by publisher] (Sourc...
Source: Carbohydrate Research - September 28, 2009 Category: Genetics & Stem Cells Authors: Roy SK, Das D, Mondal S, Maiti D, Bhunia B, Maiti TK, Islam SS Tags: Carbohydr Res Source Type: journals
Pectin: structure and function - A special issue dedicated to Professor Walter Pilnik. Editorial.
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PMID: 19755179 [PubMed - in process] (Source: Carbohydrate Research)
Source: Carbohydrate Research - September 17, 2009 Category: Genetics & Stem Cells Authors: Morris VJ Tags: Carbohydr Res Source Type: journals
Pectin: structure and function - A special issue dedicated to Professor Walter Pilnik. Editorial.
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PMID: 19755180 [PubMed - in process] (Source: Carbohydrate Research)
Source: Carbohydrate Research - September 17, 2009 Category: Genetics & Stem Cells Authors: Voragen AG Tags: Carbohydr Res Source Type: journals
Structure of a novel highly branched alpha-glucan enzymatically produced from maltodextrin.
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The bacterial strain PP710, isolated from soil and identified as Paenibacillus species, produced a low-digestibility alpha-glucan containing a large amylase-resistant portion. This alpha-glucan was obtained in high yields from maltodextrin (dextrose equivalent 3) by using the condensed culture supernatant of the strain as the enzyme preparation. The water-soluble dietary fiber content of the low-digestibility alpha-glucan was 80.2%, and showed resistance to a rat intestinal enzyme preparation. The alpha-glucan was found to be a novel highly branched alpha-glucan by acid hydrolysis, NMR analysis, gel permeation chromato...
Source: Carbohydrate Research - August 18, 2009 Category: Genetics & Stem Cells Authors: Tsusaki K, Watanabe H, Nishimoto T, Yamamoto T, Kubota M, Chaen H, Fukuda S Tags: Carbohydr Res Source Type: journals
Supramolecular hydrogels formed from biodegradable ternary COS-g-PCL-b-MPEG copolymer with alpha-cyclodextrin and their drug release.
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On the basis of the synthesis of novel biodegradable amphiphilic MPEG-b-PCL-grafted chitooligosaccharide (COS-g-PCL-b-MPEG) copolymers, supramolecular hydrogels were fabricated rapidly via their inclusion complexation with alpha-cyclodextrin (alpha-CD) in aqueous solutions. The graft copolymers were characterized by (1)H NMR spectroscopy, gel permeation chromatography (GPC), and fluorescence measurement, and the supramolecular structure of the resultant hydrogels was confirmed by X-ray diffraction measurements. Rheological studies of as-obtained hydrogels indicate that the physical properties could be modulated by cont...
Source: Carbohydrate Research - August 18, 2009 Category: Genetics & Stem Cells Authors: Zhao S, Lee J, Xu W Tags: Carbohydr Res Source Type: journals
Synthesis of monodeoxy and mono-O-methyl congeners of methyl beta-D-mannopyranosyl-(1-->2)-beta-D-mannopyranoside for epitope mapping of anti-Candida albicans antibodies.
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Synthesis of monodeoxy and mono-O-methyl congeners of methyl beta-D-mannopyranosyl-(1-->2)-beta-D-mannopyranoside for epitope mapping of anti-Candida albicans antibodies.
Carbohydr Res. 2009 Aug 17;344(12):1397-411
Authors: Nycholat CM, Bundle DR
A panel of six complementary monodeoxy and mono-O-methyl congeners of methyl beta-d-mannopyranosyl-(1-->2)-beta-d-mannopyranoside (1) were synthesized by stereoselective glycosylation of monodeoxy and mono-O-methyl monosaccharide acceptors with a 2-O-acetyl-glucosyl trichloroacetimidate donor, followed by a two-step oxidation-reduction sequence at C-2'. The beta-...
Source: Carbohydrate Research - August 15, 2009 Category: Genetics & Stem Cells Authors: Nycholat CM, Bundle DR Tags: Carbohydr Res Source Type: journals
Potent angiogenic inhibition effects of diacetylated chitohexaose separated from chitooligosaccharides and its mechanism of action in vitro.
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This study was performed to demonstrate the effects of diacetylated chitohexaose (hexamer) separated from a chitooligosaccharide (COS) mixture on tumor angiogenesis and its mechanism of action. Five fractions from dimer to hexamer were separated by a linear gradient solution of HCl on a cation-exchange resin. Then HCl was removed from the fractions by a charcoal column. The purity of the five fractions was analyzed by HPLC and the molecular masses were analyzed by MALDI-TOFMS. The hexamer expressed an inhibitory influence on CAM angiogenesis in a dose-dependent manner at concentrations of 6.25-50mug/egg. On further investi...
Source: Carbohydrate Research - July 22, 2009 Category: Genetics & Stem Cells Authors: Xiong C, Wu H, Wei P, Pan M, Tuo Y, Kusakabe I, Du Y Tags: Carbohydr Res Source Type: journals
"Carbohydr Res"; +218 new citations
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218 new pubmed citations were retrieved for your search.
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"Carbohydr Res"
These pubmed results were generated on 2009/06/27PubMed, a service of the National Library of Medicine, includes over 15 million
citations for biomedical articles back to the 1950's.
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PubMed includes links to many sites providing full text articles and other related resources. (Source: Carbohydrate Research)
Source: Carbohydrate Research - June 28, 2009 Category: Genetics & Stem Cells Tags: Report Source Type: journals
Short synthetic sequence for 2-sulfation of alpha-l-iduronate glycosides.
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We report a simple, three-step procedure for the introduction of sulfate at the 2-position starting with the methyl ester of alpha-l-iduronate glycosides. The procedure involves protection of the 2- and 4-hydroxyl groups of the iduronate moiety as the dibutyl stannylene acetal, selective sulfation with sulfur trioxide-trimethylamine, and deprotection of the methyl ester to afford the desired 2-sulfate in 61% overall yield.
PMID: 19356745 [PubMed - as supplied by publisher] (Source: Carbohydrate Research)
Source: Carbohydrate Research - March 20, 2009 Category: Genetics & Stem Cells Authors: Blanchard S, Turecek F, Gelb MH Tags: Carbohydr Res Source Type: journals
Utilization of squid pen for the efficient production of chitosanase and antioxidants through prolonged autoclave treatment.
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We have developed a culture system for efficient production of chitosanase by Bacillus sp. TKU004. TKU004 was cultivated by using squid pen powder as the sole carbon/nitrogen source. The effects of autoclave treatments of the medium on the production of chitosanase were investigated. Autoclave treatment of squid pen powder for 45min remarkably promoted enzyme productivity. When the culture medium containing an initial squid pen powder concentration of 3% was autoclaved for 45min, the chitosanase activity was optimal and reached 0.14-0.16U/mL. In addition, extracellular surfactant-stable chitosanase was purified from th...
Source: Carbohydrate Research - March 17, 2009 Category: Genetics & Stem Cells Authors: Wang SL, Wu PC, Liang TW Tags: Carbohydr Res Source Type: journals
An improved procedure for nucleoside synthesis using glycosyl trifluoroacetimidates as donors.
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Using glycosyl trifluoroacetimidates as donors and nitromethane (or acetonitrile) as solvent, silylation and subsequent glycosylation were realized in a 'one-pot' procedure to provide the corresponding nucleosides derivatives in high yields.
PMID: 19342007 [PubMed - as supplied by publisher] (Source: Carbohydrate Research)
Source: Carbohydrate Research - March 14, 2009 Category: Genetics & Stem Cells Authors: Liao J, Sun J, Yu B Tags: Carbohydr Res Source Type: journals
Synthesis of 4-O-glycosylated 1,5-anhydro-d-fructose and of 1,5-anhydro-d-tagatose from a common intermediate 2,3-O-isopropylidene-d-fructose.
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Four novel disaccharides of glycosylated 1,5-anhydro-d-ketoses have been prepared: 1,5-anhydro-4-O-beta-d-glucopyranosyl-d-fructose, 1,5-anhydro-4-O-beta-d-galactopyranosyl-d-fructose, 1,5-anhydro-4-O-beta-d-glucopyranosyl-d-tagatose, and 1,5-anhydro-4-O-beta-d-galactopyranosyl-d-tagatose. The common intermediate, 1,5-anhydro-2,3-O-isopropylidene-beta-d-fructopyranose, was prepared from d-fructose and was converted into the d-tagatose derivative by oxidation followed by stereoselective reduction to the 4-epimer. The anhydroketoses thus prepared were glycosylated and deprotected to give the disaccharides.
PMID: 1934...
Source: Carbohydrate Research - March 12, 2009 Category: Genetics & Stem Cells Authors: Agoston K, Dékány G, Lundt I Tags: Carbohydr Res Source Type: journals
Facile one-pot synthesis of sugar-quinoline derivatives.
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Seven different sugar-quinoline derivatives were synthesised in a 'one-pot' reaction from their corresponding C-beta-glycoside derivatives. The compounds were characterised by NMR spectroscopy and elemental analysis.
PMID: 19349043 [PubMed - as supplied by publisher] (Source: Carbohydrate Research)
Source: Carbohydrate Research - March 12, 2009 Category: Genetics & Stem Cells Authors: Nagarajan S, Das TM Tags: Carbohydr Res Source Type: journals
Sialic acid attenuates the cytotoxicity of the lipid hydroperoxides HpODE and HpETE.
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Reduction of peroxide molecular species is an essential function in living organisms. In previous studies, we proposed a new function for the sialic acid N-acetylneuraminic acid (Neu5Ac)-that of antioxidant/hydrogen peroxide scavenging agent. On the basis of the reaction scheme, Neu5Ac is thought to act as a general antioxidant of all hydroperoxide-type species (R-OOHs). The concentration of tert-butyl hydroperoxide (t-BuOOH) decreased after co-incubation with N-acetylneuraminic acid. Neu5Ac also decreased the R-OOH concentration in solutions of peroxylinolenic acid (13(S)-hydroperoxy-(9Z,11E)-octadecadienoic acid, HpO...
Source: Carbohydrate Research - March 11, 2009 Category: Genetics & Stem Cells Authors: Iijima R, Ichikawa T, Yamazaki M Tags: Carbohydr Res Source Type: journals
The structure of Cryptococcus neoformans galactoxylomannan contains beta-d-glucuronic acid.
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The structure of galactoxylomannan, a capsular polysaccharide from the opportunistic yeast Cryptococcus neoformans, was re-examined by NMR spectroscopy and GC-MS. The residue that is 3-linked to the side chain galactose and was previously assigned as beta-d-xylose [Vaishnav, V. V.; Bacon, B. E.; O'Neill, M.; Cherniak, R. Carbohydr. Res.1998, 306, 315-330] was determined to be beta-d-glucuronic acid. A revised structure for this polymer is presented, along with a proposal that this compound be termed glucuronoxylomannogalactan (GXMGal).
PMID: 19345342 [PubMed - as supplied by publisher] (Source: Carbohydrate Research)
Source: Carbohydrate Research - March 10, 2009 Category: Genetics & Stem Cells Authors: Heiss C, Stacey Klutts J, Wang Z, Doering TL, Azadi P Tags: Carbohydr Res Source Type: journals
Comprehensive analysis of glycosyltransferases in eukaryotic genomes for structural and functional characterization of glycans.
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In this study, we systematically investigated 36 eukaryotic genomes and obtained 3426 glycosyltransferase homologs for biosynthesis of major glycans, classified into 53 families based on sequence similarity. The families were further grouped into six functional categories based on the biosynthetic pathways, which revealed characteristic patterns among organism groups in the degree of conservation and in the number of paralogs. The results also revealed a strong correlation between the number of glycosyltransferases and the number of coding genes in each genome. We then predicted the ability to synthesize major glycan struc...
Source: Carbohydrate Research - March 9, 2009 Category: Genetics & Stem Cells Authors: Hashimoto K, Tokimatsu T, Kawano S, Yoshizawa AC, Okuda S, Goto S, Kanehisa M Tags: Carbohydr Res Source Type: journals
Chitosan-LiOH-urea aqueous solution-a novel water-based system for chitosan processing.
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A solution of partially N-deacetylated chitosan in aqueous lithium hydroxide (LiOH)/urea was prepared successfully through a freeze-thawing process and the dissolution behavior was studied. The results indicated that chitosan can directly dissolve in LiOH/urea aqueous solution. LiOH mainly contributed to the breakage of intramolecular and intermolecular hydrogen bonds in chitosan. Urea, LiOH, and chitosan formed inclusion compound (IC) with urea as the IC host, and the LiOH-chitosan complex as the guest. Aqueous 4.8wt% LiOH/8.0wt% urea was verified to be the optimal solvent for chitosan. The results of rheology and vis...
Source: Carbohydrate Research - March 9, 2009 Category: Genetics & Stem Cells Authors: Fan M, Hu Q Tags: Carbohydr Res Source Type: journals
Isolation and characterization of a novel chondroitin sulfate from squid liver integument rich in N-acetylgalactosamine(4,6-disulfate) and glucuronate(3-sulfate) residues.
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Novel chondroitin sulfate (CS) chains with an average molecular mass of 79.6kDa were purified from squid liver integument. A compositional analysis of the CS chains using chondroitinases (CSases) ABC and AC-I revealed a range of variably sulfated disaccharides with GlcAbeta1-->3GalNAc(6-sulfate), GlcAbeta1-->3GalNAc(4-sulfate), and GlcAbeta1-->3GalNAc(4,6-disulfate) as the major ones, significant amounts of rare 3-sulfated GlcA-containing disaccharides, and a small amount of nonsulfated GlcAbeta1-->3GalNAc. The CS chains exhibited neurite outgrowth-promoting activity toward embryonic mouse hippocampal neuro...
Source: Carbohydrate Research - March 5, 2009 Category: Genetics & Stem Cells Authors: Shetty AK, Kobayashi T, Mizumoto S, Narumi M, Kudo Y, Yamada S, Sugahara K Tags: Carbohydr Res Source Type: journals
Thermodynamic stabilities and conformational analyses of 4,6-O-acetalized 1,5-anhydro-5-thio-dl-threo-2-enitols.
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4,6-O-Methylidene and 4,6-O-neopentylidene derivatives of 1,5-anhydro-2,3-dideoxy-5-thio-dl-thero-hex-2-enitol having the C-inside form were found to be thermodynamically more stable than the corresponding O-inside conformers. Thermodynamic stabilities, as well as the conformation of sulfoxide and sulfone derivatives of the 4,6-O-neopentylidene compound were examined by experiment and ab initio MO and DFT calculations. These thermodynamic stabilities, and the most stable conformations determined by NMR data, were corroborated by calculations.
PMID: 19327754 [PubMed - as supplied by publisher] (Source: Carbohydrate Research)
Source: Carbohydrate Research - March 4, 2009 Category: Genetics & Stem Cells Authors: Watanabe Y, Sakakibara T Tags: Carbohydr Res Source Type: journals
Conformational studies of the capsular polysaccharide produced by Neisseria meningitidis group A.
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The effect of different cations on the conformational and morphological properties of the capsular polysaccharide produced by Neisseria meningitidis group A was investigated. Circular dichroism studies showed that the presence of Na(+), NH4+ or Ca(2+) ions induced different local conformations of the polysaccharide chain through interactions with the phosphodiester group bridging the saccharide residues in the polymer chain. Atomic force microscopy experiments confirmed that the morphology of the polysaccharide chains was different depending on the nature of the counterion. Ammonium ions were associated with the presen...
Source: Carbohydrate Research - March 4, 2009 Category: Genetics & Stem Cells Authors: Foschiatti M, Hearshaw M, Cescutti P, Ravenscroft N, Rizzo R Tags: Carbohydr Res Source Type: journals
Preparation and characterization of cationic corn starch with a high degree of substitution in dioxane-THF-water media.
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Cationic corn starch derivatives with a high degree of substitution are prepared in alkaline solution or in mixed media of organic solvent and water with different levels of the cationic reagent, 2,3-epoxypropyltrimethylammonium chloride. The starch cationization yield is investigated, and the results indicate that the degree of substitution (DS) of the samples depends on the reaction conditions and reaction media. The maximum DS values are up to 1.37 in 1,4-dioxane alkaline-aqueous solution. Meanwhile, the structures of the cationic starch derivatives are characterized by elemental analyses, FTIR spectroscopy, X-ray d...
Source: Carbohydrate Research - February 28, 2009 Category: Genetics & Stem Cells Authors: Pi-Xin W, Xiu-Li W, Xue DH, Xu K, Tan Y, Du XB, Li WB Tags: Carbohydr Res Source Type: journals
Chitosan derivatives alter release profiles of model compounds from calcium phosphate implants.
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The aim of the current study was to evaluate the impact of chitosan derivatives, namely N-octyl-chitosan and N-octyl-O-sulfate chitosan, incorporated in calcium phosphate implants to the release profiles of model drugs. The rate and extent of calcein (on M.W. 650Da) ED, and FITC-dextran (M.W. 40kDa) on in vitro release were monitored by fluorescence spectroscopy. Results show that calcein release is affected by the type of chitosan derivative used. A higher percentage of model drug was released when the hydrophilic polymer N-octyl-sulfated chitosan was present in the tablets compared with the tablets containing the hyd...
Source: Carbohydrate Research - February 28, 2009 Category: Genetics & Stem Cells Authors: Green S, Roldo M, Douroumis D, Bouropoulos N, Lamprou D, Fatouros DG Tags: Carbohydr Res Source Type: journals
Synthetic studies on the carbohydrate moiety of the antigen from the parasite Echinococcusmultilocularis.
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Stereocontrolled syntheses of branched tri-, tetra-, and pentasaccharides displaying a Galbeta1-->3GalNAc core in the glycan portion of the glycoprotein antigen from the parasite Echinococcusmultilocularis have been accomplished. Trisaccharide Galbeta1-->3(GlcNAcbeta1-->6)GalNAcalpha1-OR (A), tetrasaccharide Galbeta1-->3(Galbeta1-->4GlcNAcbeta1-->6)GalNAcalpha1-OR (D), and pentasaccharides Galbeta1-->3(Galbeta1-->4Galbeta1-->4GlcNAcbeta1-->6)GalNAcalpha1-OR (E) and Gal beta1-->3(Galalpha1-->4Galbeta1-->4GlcNAcbeta1-->6)GalNAcalpha1-OR (F) (R = 2-(trimethylsilyl)ethyl) were synt...
Source: Carbohydrate Research - February 24, 2009 Category: Genetics & Stem Cells Authors: Koizumi A, Hada N, Kaburaki A, Yamano K, Schweizer F, Takeda T Tags: Carbohydr Res Source Type: journals
Efficient and systematic synthesis of a small glycoconjugate library having human complex type oligosaccharides.
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To prepare a small library of homogeneous glycoconjugates with varying oligosaccharide structures, a combinatorial strategy was employed. The target glycopeptide was divided into two peptide segments (A and B) and both were prepared by solid phase peptide synthesis. These peptides, which can be coupled by native chemical ligation through an amide bond, were subsequently coupled to two kinds of human complex type oligosaccharides. This process systematically afforded the desired glycoconjugate library.
PMID: 19285659 [PubMed - as supplied by publisher] (Source: Carbohydrate Research)
Source: Carbohydrate Research - February 23, 2009 Category: Genetics & Stem Cells Authors: Murase T, Tsuji T, Kajihara Y Tags: Carbohydr Res Source Type: journals
Synthesis and antimicrobial activity of the Schiff base from chitosan and citral.
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Chitosan, a biocompatible, biodegradable, non-toxic polymer, is prepared from chitin, which is the second most naturally occurring biopolymer after cellulose. The Schiff base of chitosan was synthesized by the reaction of chitosan with citral working under high-intensity ultrasound. The effect of the molar ratio of chitosan to citral, reaction time, and temperature on the yield has been investigated. The optimal conditions were a temperature of 50 degrees C, a molar ratio of chitosan to citral of 1:6, and a reaction time of 10h. The maximum yield achieved was 86.4% under optimum conditions. The structure of the Schiff ...
Source: Carbohydrate Research - February 20, 2009 Category: Genetics & Stem Cells Authors: Jin X, Wang J, Bai J Tags: Carbohydr Res Source Type: journals
Structural elucidation and immuno-stimulating activity of an acidic heteropolysaccharide (TAPA1) from Tremella aurantialba.
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A novel acidic heteropolysaccharide (TAPA1) was purified from hot water extracts of Tremella aurantialba fruiting bodies by DEAE-Sepharose Fast Flow and Sephacryl S-500 High-Resolution Chromatography. The heteropolysaccharide had a molecular weight of ca. 1.35x10(6)Da, and a carbohydrate content estimated to be approximately 98.7% by the phenol-sulfuric acid method. It was composed mainly of d-mannose, d-xylose, and d-glucuronic acid in the ratio of ca. 5:4:1, along with trace amounts of d-galacturonic acid and d-glucose. Monosaccharide compositional analysis and GC-MS of methylated derivatives, combined with (1)H and ...
Source: Carbohydrate Research - February 13, 2009 Category: Genetics & Stem Cells Authors: Du X, Zhang J, Yang Y, Ye L, Tang Q, Jia W, Liu Y, Zhou S, Hao R, Gong C, Pan Y Tags: Carbohydr Res Source Type: journals
Preparation and conformational analysis of C-glycosyl beta(2)- and beta/beta(2)-peptides.
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Ten C-glycosyl beta(2)- and beta/beta(2)-peptides with three to eight amino acid residues have been prepared. Solution and solid-phase peptide syntheses were employed to assemble beta(2)-amino acids in which C-glycosylic substituents are attached to the C-2 position of beta-amino acids. Conformational analysis of the C-glycosyl beta(2)-peptides using NMR and CD spectra indicates that the tripeptide can form a helical secondary structure. Besides, helix directions of the C-glycosyl beta/beta(2)-peptides are governed by the configuration at the alpha-carbon of the peptide backbone that originates from the stereocenter of...
Source: Carbohydrate Research - January 23, 2009 Category: Genetics & Stem Cells Authors: Inaba Y, Kawakami T, Aimoto S, Ikegami T, Takeuchi T, Nakazawa T, Yano S, Mikata Y Tags: Carbohydr Res Source Type: journals
Glycoside modification of oleanolic acid derivatives as a novel class of anti-osteoclast formation agents.
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Oleanolic acid, a natural product, possesses an anti-osteoclast formation activity. Targeting at discovery of novel and potent anti-bone resorption agents, 22 glycosides of oleanolic acid derivatives (including d-galactopyranosides, d-glucopyranosides, d-xylopyranoses, d-arabopyranoses and d-glycuronic acids) were synthesized at phase-transfer-catalyzed conditions (K(2)CO(3), Bu(4)NBr, CH(2)Cl(2)-H(2)O) and their inhibitory activity on the formation of osteoclast-like multinucleated cells (OCLs) induced by 1alpha, 25-dihydroxy vitamin D(3) was evaluated in a co-culture assay system. The structure-activity relationships...
Source: Carbohydrate Research - January 23, 2009 Category: Genetics & Stem Cells Authors: Li JF, Chen SJ, Zhao Y, Li JX Tags: Carbohydr Res Source Type: journals
Synthesis of fused pyran-carbahexopyranoses as glycosidase inhibitors.
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Synthesis of polyhydroxylated oxabicyclo[4,4,0]decanes, which constitute a new family of annulated carbasugars, has been accomplished in a stereoselective manner by employing readily available 1,2-anhydro-3,4,6-tri-O-benzyl-alpha-d-glycopyranoses.
PMID: 19217083 [PubMed - as supplied by publisher] (Source: Carbohydrate Research)
Source: Carbohydrate Research - January 23, 2009 Category: Genetics & Stem Cells Authors: Doddi VR, Kancharla PK, Reddy YS, Kumar A, Vankar YD Tags: Carbohydr Res Source Type: journals
A novel supramolecular compound 2,2'-bipyridyl-phosphotungstic acid: synthesis and catalysis.
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A new supramolecular compound (C(10)H(8)N(2))(3.2).H(3)PW(12)O(40).25.6H(2)O (Bipy-PW(12)) was synthesized by self-assembly design, and characterized by elemental analysis, Fourier-transform infrared spectra (FTIR), and (31)P NMR spectra. Bipy-PW(12) can effectively catalyze oxidative degradation of chitosan with H(2)O(2) in heterogeneous phase. To obtain water-soluble chitosan with an average molecular weight of 5000, the optimum reaction conditions were determined as follows: reaction temperature, 80 degrees C; reaction time, 13min; H(2)O(2) concentration, 2.7mol/L; and mass ratio of Bipy-PW(12) to chitosan, 0.01.
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Source: Carbohydrate Research - January 19, 2009 Category: Genetics & Stem Cells Authors: Wang QS, Wang SM, Lin S Tags: Carbohydr Res Source Type: journals
Fine structural properties of natural and synthetic glycogens.
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In this study, the fine structures of ESG and NSG were analyzed using isoamylase and alpha-amylase. Isoamylase completely hydrolyzed the alpha-1,6 linkages of ESG and NSG. The unit-chain distribution (distribution of degrees of polymerization (DP) of alpha-1,4 linked chains) of ESG was slightly narrower than that of NSG. alpha-Amylase treatment revealed that initial profiles of hydrolyses of ESG and NSG were almost the same: both glycogens were digested slowly, compared with starch. The final products from NSG by alpha-amylase hydrolysis were glucose, maltose, maltotriose, branched oligosaccharides with DP4, and highly bra...
Source: Carbohydrate Research - January 19, 2009 Category: Genetics & Stem Cells Authors: Takata H, Kajiura H, Furuyashiki T, Kakutani R, Kuriki T Tags: Carbohydr Res Source Type: journals
Characterization of the interaction between 2'-deoxyuridine and human serum albumin.
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The binding of 2'-deoxyuridine to human serum albumin (HSA) was investigated by fluorescence spectroscopy in combination with molecular modeling under simulation of physiological conditions. The quenching mechanism was suggested to be static according to the fluorescence measurement. The thermodynamic parameters: enthalpy change (DeltaH) and entropy change (DeltaS) were calculated to be -18.87kJ/mol and 24.00J/(molK) according to the Vant'Hoff equation. These data suggest that hydrophobic interactions are the predominant intermolecular forces stabilizing the complex. Experimental results are in agreement with the resul...
Source: Carbohydrate Research - January 19, 2009 Category: Genetics & Stem Cells Authors: Cui F, Yan Y, Zhang Q, Du J, Yao X, Qu G, Lu Y Tags: Carbohydr Res Source Type: journals
Production of xylooligosaccharides by controlled acid hydrolysis of lignocellulosic materials.
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Different agricultural wastes, namely tobacco stalk (TS), cotton stalk (CS), sunflower stalk (SS), and wheat straw (WS), were used for the production of xylooligosaccharide (XO). XO production was performed by acid hydrolysis of xylan, which was obtained by alkali extraction from these agricultural wastes. The major component of these agricultural wastes was determined as cellulose (30-42%), followed by xylan (20%) and lignin (20-27%). Xylans from these wastes had mainly xylose (85-96%) with small amount of glucose, while wheat straw xylan contained also arabinose. The best xylan conversion into XOs was achieved with 0...
Source: Carbohydrate Research - January 19, 2009 Category: Genetics & Stem Cells Authors: Akpinar O, Erdogan K, Bostanci S Tags: Carbohydr Res Source Type: journals
Endo-beta-N-acetylglucosaminidase-catalyzed polymerization of beta-Glcp-(1-->4)-GlcpNAc oxazoline: a revisit to enzymatic transglycosylation.
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Endo-beta-N-acetylglucosaminidase-catalyzed polymerization of beta-Glcp-(1-->4)-GlcpNAc oxazoline: a revisit to enzymatic transglycosylation.
Carbohydr Res. 2009 Jan 19;
Authors: Ochiai H, Huang W, Wang LX
An alternative synthesis of beta-Glcp-(1-->4)-GlcpNAc oxazoline is described, and its enzymatic reaction with the endo-beta-N-acetylglucosaminidase from Arthrobacter protophormiae (Endo-A) was re-investigated. Under normal transglycosylation conditions with a catalytic amount of enzyme, Endo-A showed only marginal activity for transglycosylation with the disaccharide oxazoline, consistent with our previ...
Source: Carbohydrate Research - January 19, 2009 Category: Genetics & Stem Cells Authors: Ochiai H, Huang W, Wang LX Tags: Carbohydr Res Source Type: journals
X-ray structure of a sodium salt of digeneaside isolated from red alga Ceramium botryocarpum.
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X-ray diffraction analysis has been recently used to determine the crystal structure of the floridoside (2-O-alpha-d-galactopyranosylglycerol) isolated from red alga Palmaria palmata and Dilsea carnosa, respectively [Simon-Colin, C.; Michaud, F.; Léger, J.-M.; Deslandes, E. Carbohydr. Res.2003, 338, 2413-2416; Vonthron-Senechau, C.; Sopkova-de Oliveira Santos. J.; Mussio, I.; Rusig, A. M. Carbohydr. Res. 2008, 343, 2697-2698]. In this present study, a similar analysis was performed on another compound belonging to the glycopyranosyl-glycerols family present in red algae, digeneaside. The crystal structure of a hyd...
Source: Carbohydrate Research - January 17, 2009 Category: Genetics & Stem Cells Authors: Claude A, Bondu S, Michaud F, Bourgougnon N, Deslandes E Tags: Carbohydr Res Source Type: journals
Structure of the O-polysaccharide from the lipopolysaccharide of Providencia alcalifaciens O31 containing an ether of d-mannose with (2R,4R)-2,4-dihydroxypentanoic acid.
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Recently, ether-linked diastereomeric 2,4-dihydroxypentanoic acids have been reported as new components of bacterial glycans [Shashkov, A. S. et al.Nat. Prod. Commun.2008, 3, 1625-1630]. In this work, an ether of (2R,4R)-2,4-dihydroxypentanoic acid (Dhpa) with d-mannose was identified in the O-polysaccharide of Providencia alcalifaciens O31, and the polysaccharide structure was elucidated. Studies by NMR spectroscopy confirmed the ether linkage between O-2 of Dhpa and O-4 of Man, and the absolute configuration of Man was determined after ether cleavage with boron trichloride. In the polysaccharide, Dhpa was found to ex...
Source: Carbohydrate Research - January 16, 2009 Category: Genetics & Stem Cells Authors: Ovchinnikova OG, Kocharova NA, Shashkov AS, Bialczak-Kokot M, Knirel YA, Rozalski A Tags: Carbohydr Res Source Type: journals
Design and synthesis of glucose-templated proline-lysine chimera: polyfunctional amino acid chimera with high prolyl cis amide rotamer population.
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We describe the synthesis of two glucose-templated proline-lysine chimeras (GlcTProLysCs) that differ in the stereochemistry of the hydroxymethyl substituent at the C-5' position of the pyrrolidine ring. The key synthetic steps involve C-glycosylation of an exocyclic glucose-based epoxide with allyltributylstannane, which affords functionalized C-ketosides containing an alpha-hydroxy ester moiety; introduction of an amino group at C-2 through stereoselective reductive amination; and regioselective installation of the azide group at C-6 on the glucose scaffold. Incorporation of these chimeras into the model peptides Ac-GlcT...
Source: Carbohydrate Research - January 3, 2009 Category: Genetics & Stem Cells Authors: Zhang K, Schweizer F Tags: Carbohydr Res Source Type: journals
GROMOS96 43a1 performance on the characterization of glycoprotein conformational ensembles through molecular dynamics simulations.
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Considering the small number of papers assessing the conformational profile of glycoproteins through molecular dynamics (MD) simulations, the current work reports on a systematic analysis of the performance of the GROMOS96 43a1 force field and Löwdin HF/6-31G( * *)-derived atomic charges in the conformational description of glycoproteins. The results substantiate the accuracy of the computational representation of glycoprotein conformational ensembles in aqueous solution based on their agreement to available experimental information, supporting further contributions of computational techniques, mainly MD, in futur...
Source: Carbohydrate Research - January 3, 2009 Category: Genetics & Stem Cells Authors: Pol-Fachin L, Fernandes CL, Verli H Tags: Carbohydr Res Source Type: journals
Efficient synthesis and protein conjugation of beta-(1-->6)-d-N-acetylglucosamine oligosaccharides from the polysaccharide intercellular adhesin.
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Efficient synthesis and protein conjugation of beta-(1-->6)-d-N-acetylglucosamine oligosaccharides from the polysaccharide intercellular adhesin.
Carbohydr Res. 2009 Jan 3;
Authors: Leung C, Chibba A, Gómez-Biagi RF, Nitz M
A wide variety of medically important biofilm forming bacteria produce similar polysaccharide intracellular adhesins (PIAs). The PIA structures consist of partially de-N-acetylated beta-(1-->6)-N-acetylglucosamine polymers. These exopolysaccharides are key components of the bacterial biofilm matrix. Here, we describe the efficient synthesis of PIA oligosaccharides using an acid re...
Source: Carbohydrate Research - January 3, 2009 Category: Genetics & Stem Cells Authors: Leung C, Chibba A, Gómez-Biagi RF, Nitz M Tags: Carbohydr Res Source Type: journals
Carbasugar-thioether pseudodisaccharides related to N-glycan biosynthesis.
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Analogues of the alpha-Glcp-(1-->3)-alpha-Glcp and alpha-Glcp-(1-->3)-alpha-Manp disaccharides (representing the two alpha-gluco linkages cleaved by alpha-Glucosidase II in N-glycan biosynthesis) in which the non-reducing-end sugar is replaced by a carbasugar and the inter-glycosidic oxygen by a sulfur were synthesised. The key coupling step was an S(N)2 displacement of an equatorial triflate at C-1 of the carbasugar by C-3 gluco or manno thiolates with inversion of configuration to give thioether pseudodisaccharides with axial substitution at C-1 of the carbasugar. The deprotected pseudodisaccharides failed to i...
Source: Carbohydrate Research - January 3, 2009 Category: Genetics & Stem Cells Authors: Cumpstey I, Alonzi DS, Butters TD Tags: Carbohydr Res Source Type: journals
