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Carbohydrate Research

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https://www.readbyqxmd.com/read/28728011/anti-inflammatory-effect-of-sugar-amino-acid-maillard-reaction-products-on-intestinal-inflammation-model-in%C3%A2-vitro-and-in%C3%A2-vivo
#1
Jun-Gu Oh, Su-Hyun Chun, Da Hyun Kim, Jin Hye Kim, Hye Soo Shin, Yong Soo Cho, Yong Ki Kim, Hee-Don Choi, Kwang-Won Lee
The Maillard reaction is a nonenzymatic reaction between an amino acid and a reducing sugar that usually occurs upon heating. This reaction occurs routinely in cooking, generates numerous products, which are collectively referred to as Maillard reaction products (MRPs) contributing to aroma and color features. Advanced glycation end-products (AGEs) transformed from MRPs are participated in many types of inflammation reaction. In this study, various sugar-amino acid MRPs were prepared from three different amino acids (lysine, arginine, and glycine) and sugars (glucose, fructose, and galactose) for 1 h with heating at 121 °C...
July 11, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28734224/structural-characterization-of-glucosylated-lactose-derivatives-synthesized-by-the-lactobacillus-reuteri-gtfa-and-gtf180-glucansucrase-enzymes
#2
Hien T T Pham, Lubbert Dijkhuizen, Sander S van Leeuwen
Glucansucrase enzymes from lactic acid bacteria are receiving strong interest because of their wide range of gluco-oligosaccharide and polysaccharide products from sucrose, some of which have prebiotic potential. Glucansucrases GtfA and Gtf180 from Lactobacillus reuteri strains are known to convert sucrose into α-glucans with different types of linkages, but also to use other molecules as acceptor substrates. Here we report that incubation of (N-terminally truncated versions of) these enzymes with lactose plus sucrose resulted in synthesis of at least 5 glucosylated lactose products of a degree of polymerization (DP) of 3-4...
July 8, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28686930/characterization-of-the-o-antigen-polysaccharide-derived-from-pantoea-agglomerans-ig1-lipopolysaccharide
#3
Masahito Hashimoto, Rune Satou, Mami Ozono, Hiroyuki Inagawa, Gen-Ichiro Soma
A polysaccharide fraction was isolated from the Pantoea agglomerans IG1 lipopolysaccharide (IP-PA1), and its O-antigenic polysaccharide was characterized by chemical analyses and 1D and 2D (1)H and (13)C NMR spectroscopy. The polysaccharide is composed of linear tetrasaccharide repeating units, consisting of glucose and rhamnose, where 40% of one of the rhamnose residues is substituted with glucose: →2)-α-l-Rhap-(1→6)-α-d-Glcp-(1→2)-[β-d-Glcp-(1→3)]0.4-α-l-Rhap-(1→2)-α-l-Rhap-(1→.
June 28, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28683274/sulfated-polysaccharides-of-the-vietnamese-brown-alga-sargassum-aquifolium-fucales-sargassaceae
#4
Maria I Bilan, Nadezhda E Ustyuzhanina, Alexander S Shashkov, Thi Thu Thuy Thanh, Minh Ly Bui, Thi Thanh Van Tran, Van Nguyen Bui, Anatolii I Usov
A fucoidan preparation named FSA was isolated from the brown alga Sargassum aquifolium collected from the coastal waters of Vietnam. l-Fucose, d-galactose, d-mannose, d-glucuronic acid, d-xylose, and sulfate were found to be the main constituents of FSA. The preparation was fractionated by anion-exchange chromatography on DEAE-Sephacel eluted stepwise with 0.5, 1.0, 1.5, and 2.0 M NaCl to give four fractions differing in monosaccharide composition and degree of sulfation. Their NMR spectra were too complex to be completely interpreted...
June 27, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28669498/imaging-of-protein-specific-glycosylation-by-glycan-metabolic-tagging-and-in-situ-proximity-ligation
#5
Xuexia Li, Xuecheng Jiang, Xiaoyan Xu, Chenggang Zhu, Wen Yi
Glycosylation is an important posttranslational modification, which regulates a number of critical biological processes including cell-cell recognition, signal transduction and disease progression. Probing the glycosylation status on a specific protein of interest enables an in-depth understanding of the role of glycosylation on protein structure and function. However, methods for monitoring protein-specific glycosylation are largely lacking. Here we describe a highly sensitive fluorescence imaging strategy to visualize the protein-specific glycosylation by combining glycan metabolic tagging and in situ proximity ligation (termed GPLA)...
June 27, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28688271/agarose-based-large-molecular-systems-synthesis-of-fluorescent-aromatic-agarose-amino-acid-nano-conjugates-their-ph-stimulated-structural-variations-and-interactions-with-bsa
#6
Atul K Sharma, Nishith A Chudasama, Kamalesh Prasad, A K Siddhanta
Two new nano-sized fluorescent 6-amino agarose naphthalic acid half ester derivatives were synthesized (ca.60% yields) employing 1,8- and 2,3-naphthalic acid anhydrides (1,8-AANE, and 2,3-AANE respectively). These large nano molecular frameworks (DLS 3 & 100 nm, and 3 & 152 nm respectively) contains amino, naphthalate half-ester carboxyl groups at the C-6 positions of the 1,3-β-D-galactopyranose moieties of the agarose backbone (overall DS 0.94). Structures were characterized (FT-IR, and (13)C &(1)H NMR spectrometries)...
June 26, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28672164/n-glycan-structures-of-%C3%AE-hlh-subunit-of-helix-lucorum-hemocyanin
#7
Lyudmila Velkova, Pavlina Dolashka, Jozef Van Beeumen, Bart Devreese
The carbohydrate structures of molluscan hemocyanins have recently received particular interest due to their specific monosaccharide composition, as well as their immunostimulatory properties and application in clinical studies. For the first time, we investigated N-glycans of the structural subunit β-HlH of hemocyanin isolated from Helix lucorum. In total, 32 different glycans were enzymatically liberated and characterized by tandem mass spectrometry using a Q-Trap mass spectrometer. Our study revealed a highly heterogeneous mixture of glycans with composition Hex3-7HexNAc2-5MeHex0-4Pent0-1Fuc0-1...
June 22, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28712648/elucidating-biochemical-features-and-biological-roles-of-streptomyces-proteins-recognizing-crystalline-chitin-and-cellulose-types-and-their-soluble-derivatives
#8
Hildgund Schrempf
Pioneering biochemical, immunological, physiological and microscopic studies in combination with gene cloning allowed uncovering previously unknown genes encoding proteins of streptomycetes to target crystalline chitin and cellulose as well as their soluble degradation-compounds via binding protein dependent transporters. Complementary analyses provoked an understanding of novel regulators governing transcription of selected genes. These discoveries induced detecting close and distant homologues of former orphan proteins encoded by genes from different bacteria...
June 20, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28672165/hydrogenolytic-cleavage-of-naphthylmethyl-ethers-in-the-presence-of-sulfides
#9
Philip O Adero, Dean R Jarois, David Crich
With the aid of a series of model thioether or thioglycoside containing polyols protected with combinations of benzyl ethers and 2-naphthylmethyl ethers it is demonstrated that the latter are readily cleaved selectively under hydrogenolytic conditions in the presence of the frequently catalyst-poisoning sulfides. These results suggest the possibility of employing 2-naphthylmethyl ethers in place of benzyl ethers in synthetic schemes when hydrogenolytic deprotection is anticipated in the presence of thioether type functionality...
June 20, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28662407/role-of-the-triple-solute-ion-water-interactions-on-the-saccharide-hydration-a-volumetric-approach
#10
J Teychené, H Roux-De Balmann, S Galier
The aim of this study is to further the understanding of the mechanisms that govern the hydration behavior of neutral solutes, with respect to the ions' properties that are present in a solution. For that, a systematic volumetric study of saccharides (xylose, glucose and sucrose), in the presence of various electrolytes (LiCl, NaCl, KCl, Na2SO4, K2SO4, CaCl2, MgCl2, MgSO4) has been carried out with density measurements at 298.15 K. From this data, the standard transfer molar volume of the saccharide ΔVϕ,S(0), which characterizes the hydration state of the solute, has been determined...
June 20, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28662408/a-quantitative-method-for-analyzing-glycome-profiles-of-plant-cell-walls
#11
Sivakumar Pattathil, Miles W Ingwers, Doug P Aubrey, Zenglu Li, Joseph Dahlen
Glycome profiling allows for the characterization of plant cell wall ultrastructure via sequential extractions and subsequent detection of specific epitopes with a suite of glycan-specific monoclonal antibodies (mAbs). The data are often viewed as the amount of materials recovered and coinciding colored heatmaps of mAb binding are generated. Interpretation of these data can be considered qualitative in nature as it depends on detecting subtle visual differences in antibody binding strength. Here, we report a mixed model-based quantitative approach for glycome profile analyses, which accounts for the amount of materials recovered and displays the normalized values in revised heatmaps and statistical heatmaps depicting significant differences...
June 19, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28672166/structures-and-gene-clusters-of-the-o-antigens-of-escherichia-albertii-o3-o4-o6-and-o7
#12
Olesya I Naumenko, Han Zheng, Sof'ya N Senchenkova, Hong Wang, Qun Li, Alexander S Shashkov, Jianping Wang, Yuriy A Knirel, Yanwen Xiong
The O-specific polysaccharides (OPSs) called O-antigens were obtained by mild acid degradation of the lipopolysaccharides of Escherichia albertii serotypes O3, O4, O6, and O7 and studied by sugar analysis along with 1D and 2D (1)H and (13)C NMR spectroscopy. The following structure was established for the OPS of E. albertii O4, which, to our knowledge, is unique among known bacterial polysaccharide structures: →2)-α-l-Rhap-(1 → 2)-α-l-Fucp-(1 → 2)-β-d-Galp-(1 → 3)-α-d-GalpNAc-(1 → 3)-β-d-GlcpNAc-(1→ The OPS structure of the strain of E...
June 17, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28651243/structure-of-the-lps-o-chain-from-fusobacterium-nucleatum-strain-12230
#13
Evgeny Vinogradov, Frank St Michael, Andrew D Cox
Fusobacterium nucleatum is an anaerobic bacterium found in the human mouth where it causes periodontitis. It was also found in colorectal cancer tissues and is linked with pregnancy complications, including pre-term and still births. Cell surface structures of the bacterium could be implicated in pathogenesis. Here we report the following structure of the lipopolysaccharide O-chain of F. nucleatum strain 12230: -6-α-d-Glc-4-β-d-GlcNHBu3NHBuA-3-β-d-QuiNAc4NABu- where ABu and HBu indicate (R)-3-aminobutanoyl and (R)-3-hydroxybutanoyl, respectively; all monosaccharides are in the pyranose form...
June 16, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28645002/synthesis-of-s-linked-trisaccharide-glycal-of-derhodinosylurdamycin-a-discovery-of-alkyl-thiocyanate-as-an-efficient-electrophile-for-stereoselective-sulfenylation-of-2-deoxy-glycosyl-lithium
#14
Padam P Acharya, Kedar N Baryal, Cristin E Reno, Jianglong Zhu
Stereoselective synthesis of S-linked trisaccharide glycal of angucycline antitumor antibiotic derhodinosylurdamycin A is described. The synthesis has been accomplished employing our previously reported umpolung S-glycosylation strategy - stereoselective sulfenylation of 2-deoxy glycosyl lithium. It was found that sugar-derived thiocyanate was a better electrophile than corresponding asymmetric disulfide in this type of stereoselective sulfenylation.
June 15, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28633071/structural-characterization-of-the-immunostimulatory-exopolysaccharide-produced-by-leuconostoc-mesenteroides-strain-ntm048
#15
Chiaki Matsuzaki, Chikahiro Takagaki, Yusuke Tomabechi, Lennart S Forsberg, Christian Heiss, Parastoo Azadi, Kenji Matsumoto, Toshihiko Katoh, Koji Hosomi, Jun Kunisawa, Kenji Yamamoto, Keiko Hisa
The exopolysaccharide (EPS) produced by probiotic Leuconostoc mesenteroides subsp. mesenteroides strain NTM048 has been reported to be an immunostimulant that enhances mucosal IgA production. In this study, we found that intranasal administration of mice with the EPS and an antigen (ovalbumin) resulted in secretion of antigen-specific IgA and IgG in the airway mucosa and the serum, suggesting that the EPS has the adjuvant activity for use with mucosal vaccination. Methylation analysis coupled to GC-MS, and 1D and 2D NMR spectroscopy revealed that 94% of the EPS consists of an α-(1 → 6) glucan containing 4% of 1→3-linked α-glucose branches...
June 15, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28628892/structural-characterization-of-wall-and-lipidated-polysaccharides-from-clostridium-perfringens-atcc-13124
#16
Evgeny Vinogradov, Annie Aubry, Susan M Logan
Cell surface polysaccharides produced by C. perfringens ATCC 13124 were analyzed using NMR, chemical and immunological methods. Two distinct polymers were identified. The more abundant PS1 had a structure based on a polymer of β-mannosamine with a number of modifications, including varying levels of substitution at O-6 with PEtN, N-acetylation, and different linkages between monosaccharides. The shortest variant of PS1 represented a lipoteichoic acid. It contained only 1-4-linkages between ManNAc residues, minor branching α-Ribf, and glucosyl-glycerol at the reducing end, which was acylated with linear saturated fatty acids C16, C18, and C20 (dominant)...
June 15, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28628891/synthesis-and-antimicrobial-activity-of-6-sulfo-6-deoxy-d-glucosamine-and-its-derivatives
#17
Kornelia Skarbek, Iwona Gabriel, Piotr Szweda, Marek Wojciechowski, Muna A Khan, Boris Görke, Sławomir Milewski, Maria J Milewska
6-Sulfo-6-deoxy-D-glucosamine (GlcN6S), 6-sulfo-6-deoxy-D-glucosaminitol (ADGS) and their N-acetyl and methyl ester derivatives have been synthesized and tested as inhibitors of enzymes catalyzing reactions of the UDP-GlcNAc pathway in bacteria and yeasts. GlcN6S and ADGS at micromolar concentrations inhibited glucosamine-6-phosphate (GlcN6P) synthase of microbial origin. The former was also inhibitory towards fungal GlcN6P N-acetyl transferase, but at millimolar concentrations. Both compounds and their N-acetyl derivatives exhibited antimicrobial in vitro activity, with MICs in the 0...
June 12, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28623737/rumpictuside-a-unusual-9-10-anthraquinone-glucoside-from-rumex-pictus-forssk
#18
Walaa A El-Kashak, Abdelsamed I Elshamy, Tarik A Mohamed, Abd El-Nasser G El Gendy, Ibrahim A Saleh, Akemi Umeyama
A new 8-ionized hydroxylated 9,10-anthraquinone namely, 1-hydroxy-3-methyl-9,10-anthraquinone-6-O-β-D-glucopyranoside-8-olate (Rumpictuside A, 1) along with five known flavonoids, apigenin 7-O-β-D-glucoside (2), vitexin (3), quercetin 3-O-β-D-glucouronide (4), orientin (5), and isorientin (6) were isolated from Rumex pictus. The structures of isolated compounds were identified by the extensive spectroscopic techniques such as, UV, FT-IR, 1D, 2D NMR and HR-FAB-ESI-MS. The ionized hydroxyl group in the new anthraquinone (1) was rarely found for anthraquinone glycosides isolated from natural sources...
June 9, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28623735/biochemical-and-structural-characterization-of-penicillium-purpurogenum-%C3%AE-d-galactosidase-binding-of-galactose-to-an-alternative-pocket-may-explain-enzyme-inhibition
#19
Luis Morales-Quintana, Carolina Faúndez, Raúl Herrera, Vasni Zavaleta, María Cristina Ravanal, Jaime Eyzaguirre, María Alejandra Moya-León
The fungus Penicillium purpurogenum degrades plant cell walls by the action of cellulolytic, xylanolytic and pectinolytic enzymes. The α-D-galactosidase is one of the enzymes which may act on pectin degradation. This enzyme has several biotechnological and medical applications. The aim of this work was to better understand the molecular mechanism of α-D-galactosidase from P. purpurogenum (GALP1). For this purpose, a gene coding for the enzyme was identified from the fungal genome and heterologously expressed in Pichia pastoris...
June 9, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28645003/structure-and-gene-cluster-of-the-o-antigen-of-enterobacter-cloacae-c4115
#20
Andrei V Perepelov, Guangnan Xu, Andrei V Filatov, Xinjie Zhang, Alexander S Shashkov, Min Wang, Yuriy A Knirel
An O-polysaccharide was isolated by mild acid degradation of the lipopolysaccharide of Enterobacter cloacae C4115 and studied by sugar analysis along with 1D and 2D (1)H and (13)C NMR spectroscopy. The following structure of the linear pentasaccharide repeating unit of the O-polysaccharide was established: →2)-α-l-Rhap-(1 → 2)-α-l-Rhap-(1 → 2)-α-l-Rhap-(1 → 2)-α-d-Galp-(1 → 3)-α-d-FucpNAc-(1→ The O-antigen gene cluster of E. cloacae C4115 was sequenced. The gene functions were tentatively assigned by comparison with sequences in the available databases and found to be in consistence with the O-polysaccharide structure...
June 3, 2017: Carbohydrate Research
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