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Carbohydrate Research

Alexandr S Antonov, Anatoly I Kalinovsky, Shamil S Afiyatullov, Elena V Leshchenko, Pavel S Dmitrenok, Ekaterina A Yurchenko, Vladimir I Kalinin, Valentin A Stonik
Seven new triterpene glycosides, erylosides F8 (1), V1 (2), V2 (3), V3 (4), W (5), W1 (6) and W2 (7), were isolated from a Carribean sponge Erylus goffrilleri collected from the Carribean Sea near the Arrecife-Seco reef (Cuba). Structures of the glycosides were determined using (1)H and (13)C NMR spectroscopy, including 2D NMR procedures ((1)H-(1)H COSY, (1)H-(13)С HMBC, (1)H-(13)С HSQC and NOESY) and HR ESI mass spectrometry. Erylosides 1 and 4 have 14-carboxy-24,25-dimethyllanost-8(9)-en-3β,25-diol as aglycone whereas glycosides 2, 3, 5, 6 and 7 are 14-carboxy-24-acetoxy-24-methyllanost-8(9)-en-3β-ol glycoconjugates...
August 4, 2017: Carbohydrate Research
Deqin Cai, Chaochao Xun, Feng Tang, Xiaobo Tian, Liyun Yang, Kan Ding, Wenzhe Li, Zhiping Le, Wei Huang
Glyco-PAMAM dendrimers and glyco-agarose beads bearing a core-fucosylated N-glycan trisaccharide GlcNAcβ1,4(Fucα1,6)GlcNAc or a non-fucose disaccharide GlcNAcβ1,4GlcNAc were successfully synthesized and characterized by monosaccharide analysis with HPAEC-PAD technique. These glycoconjugates as fucose lectin probes were applied in fucose-specific lectin detection and purification. The model fucose lectin AAL indicated binding activity with the FITC-labeled PAMAM carrying core-fucose trisaccharide. An affinity chromatography column stuffed with the agarose beads carrying core-fucosylated trisaccharide exhibited a good specificity in purification of AAL than non-fucose disaccharide agarose beads...
August 3, 2017: Carbohydrate Research
Chuan-Yang Zhang, Jian-Guang Luo, Rui-Huan Liu, Ru Lin, Ming-Hua Yang, Ling-Yi Kong
Seven sucrose esters, physakengoses K-Q (1-7) were isolated from the aerial parts of Physalis alkekengi var. franchetii. Their structures were elucidated on the basis of extensive spectroscopic analyses and chemical methods. These new compounds were tested for their antimicrobial abilities against Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa and Escherichia coli. Among the isolated sucrose esters, compounds 1-5 showed potent antibacterial activity with MIC values ranging from 2.16 to 12...
July 28, 2017: Carbohydrate Research
Andrey S Dmitrenok, Galina M Streshinskaya, Elena M Tul'skaya, Natalia V Potekhina, Sof'ya N Senchenkova, Alexander S Shashkov, Maria I Bilan, Irina P Starodumova, Olga V Bueva, Lyudmila I Evtushenko
The cell walls of two strains of the genus Promicromonospora (phylum Actinobacteria) were found to include non-phosphorylated anionic glycopolymers with pyruvic acid acetals of R-configuration. The cell wall of the type strain P. citrea 665(T) contains two glycopolymers of the sort, including the Kdn-teichulosonic acid with the repeating unit →6)-α-d-Gl≿p/→6)-α-d-Gl≿p3SO3(-)-(1 → 4)-α-[7,9Pyr]-Kdn-(2→, and the galactan with the repeating unit →3)-α-[4,6Pyr]-d-Galp-2OAc-(1 → . The cell wall of Promicromonospora sp...
July 27, 2017: Carbohydrate Research
Jiaojiao Lu, Chunqing Ai, Li Guo, Yinghuan Fu, Chunyang Cao, Shuang Song
Because the glycosidic linkage of uronic acid is most resistant to acid, oligosaccharides may be formed during the acid hydrolysis of acidic polysaccharides. To take chondroitin sulfate (CS) as an example of acidic polysaccharides, the present study characterized the oligosaccharides released through acid hydrolysis and demonstrated their usefulness for structural confirmation. Acid hydrolysates of commercial standard CSs from shark cartilage and porcine bone were elucidated using HPLC-MS(n) after 1-phenyl-3-methyl-5-pyrazolone (PMP) derivatization, and altogether 11 di-, tri- and tetra-saccharides with or without sulfate/acetyl groups were identified by their multi-stage mass spectra...
July 26, 2017: Carbohydrate Research
Devaraj Somasundaram, Kalpattu K Balasubramanian, Shanmugasundaram Bhagavathy
The stereochemical course of O-glycosidation of 1,2-α-d-anhydrosugars (glycal epoxides) with phenols can be tuned by varying the metal ion of the base. While the reaction of 1,2-α-d-anhydrosugars with phenols mediated by trimethylaluminium leads exclusively to 1,2-cis-α-O-aryl glycosides, similar reaction mediated by caesium carbonate gives exclusively 1,2-trans-β-O-aryl glycosides. In contrast, reaction with phenoxides generated from Grignard reagent and calcium salts affords mixture of the anomers.
July 25, 2017: Carbohydrate Research
Ellis C O'Neill, Giulia Pergolizzi, Clare E M Stevenson, David M Lawson, Sergey A Nepogodiev, Robert A Field
The GH94 glycoside hydrolase cellodextrin phosphorylase (CDP, EC produces cellodextrin oligomers from short β-1→4-glucans and α-D-glucose 1-phosphate. Compared to cellobiose phosphorylase (CBP), which produces cellobiose from glucose and α-D-glucose 1-phosphate, CDP is biochemically less well characterised. Herein, we investigate the donor and acceptor substrate specificity of recombinant CDP from Ruminiclostridium thermocellum and we isolate and characterise a glucosamine addition product to the cellobiose acceptor with the non-natural donor α-D-glucosamine 1-phosphate...
July 21, 2017: Carbohydrate Research
Wenhui Zhang, Toby Turney, Ivana Surjancev, Anthony S Serianni
Milligram quantities of α-D-ribofuranosyl 1-phosphate (sodium salt) (αR1P) were prepared by the phosphorolysis of inosine, catalyzed by purine nucleoside phosphorylase (PNPase). The αR1P was isolated by chromatography in >95% purity and characterized by (1)H and (13)C NMR spectroscopy. Aqueous solutions of αR1P were stable at pH 6.4 and 4 °C for several months. The isolated αR1P was N-glycosylated with different nitrogen bases (adenine, guanine and uracil) using PNPase or uridine phosphorylase (UPase) to give the corresponding ribonucleosides in high yield based on the glycosyl phosphate...
July 20, 2017: Carbohydrate Research
Brian C Pierce, Jane Wittrup Agger, Zhenghong Zhang, Jesper Wichmann, Anne S Meyer
Lytic polysaccharide monooxygenases (LPMOs) are copper-dependent enzymes capable of the oxidative breakdown of polysaccharides. They are of industrial interest due to their ability to enhance the enzymatic depolymerization of recalcitrant substrates by glycoside hydrolases. In this paper, twenty-four lytic polysaccharide monooxygenases (LPMOs) expressed in Trichoderma reesei were evaluated for their ability to oxidize the complex polysaccharides in soybean spent flakes, an abundant and industrially relevant substrate...
July 18, 2017: Carbohydrate Research
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
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
Daichi Hayakawa, Yoshiharu Nishiyama, Karim Mazeau, Kazuyoshi Ueda
Crystal models of cellulose Iβ and II, which contain various hydrogen bonding (HB) networks, were analyzed using density functional theory and Car-Parrinello molecular dynamics (CPMD) simulations. From the CPMD trajectories, the power spectra of the velocity correlation functions of hydroxyl groups involved in hydrogen bonds were calculated. For the Iβ allomorph, HB network A, which is dominant according to the neutron diffraction data, was stable, and the power spectrum represented the essential features of the experimental IR spectra...
July 5, 2017: Carbohydrate Research
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
Tatiana V Tyrtysh, Elena Yu Korchagina, Ivan M Ryzhov, Nicolai V Bovin
Gram scale synthesis of A (type 2) and B (type 2) tetrasaccharides in the form of 3-aminopropyl glycosides is proposed starting from 3-O-benzoyl-1,6-anhydro-N-acetylglucosamine. Its galactosylation followed by re-protection gave lactosamine derivative with single free 2'-OH group in total yield 75%. Standard fucosylation and next run of re-protection in total yield 88% gave a trisaccharide Fuc-Gal-anhydroGlcNAc with single free 3'-OH group. Its standard α-galactosylation gave protected B (type 2) tetrasaccharide...
June 27, 2017: Carbohydrate Research
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
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
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
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
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
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
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