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Carbohydrate Research

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https://www.readbyqxmd.com/read/28934626/stereoselective-sialylation-with-o-trifluoroacetylated-thiosialosides-hydrogen-bonding-involved
#1
Nikita M Podvalnyy, Nelly N Malysheva, Maria V Panova, Alexander I Zinin, Alexander O Chizhov, Anna V Orlova, Leonid O Kononov
A series of novel sialyl donors containing O-trifluoroacetyl (TFA) groups at various positions was synthesized. The choice of protecting groups in sialyl donors was based on hypothesis that variations in ability of different acyl groups to act as hydrogen bond acceptors would influence the supramolecular structure of reaction mixture (solution structure), hence the outcome of sialylation. These glycosyl donors were examined in the model glycosylation of the primary hydroxyl group of 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose in comparison with sialyl donors without O-TFA groups...
September 8, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28917967/synthesis-of-a-trisaccharide-repeating-unit-of-the-o-antigen-from-burkholderia-cenocepacia-and-its-dimer
#2
Ningning Bi, Chenghe Xiong, Guoxia Jin, Zhongwu Guo, Guofeng Gu
The trisaccharide repeating unit of an O-antigen derived from Burkholderia cenocepacia and its dimer, i.e., α-L-Rhap-(1 → 3)-α-D-GalpNAc-(1 → 3)-β-D-GalpNAc-O(CH2)3N3 (1) and α-L-Rhap-(1 → 3)-α-D-GalpNAc-(1 → 3)-β-D-GalpNAc-(1 → 4)-α-L-Rhap-(1 → 3)-α-D-GalpNAc-(1 → 3)-β-D-GalpNAc-O(CH2)3N3 (2), respectively, were synthesized via a highly convergent strategy. Glycosylation of galactosaminyl acceptor 4 with galactosaminyl trichloroacetimidate donor 5 was followed by condensation of resulting disaccharide acceptor 12 with rhamnosyl imidate donor 6 to furnish stereoselectively trisaccharyl thioglycoside 3, which was used as a key and common glycosyl donor for the construction of both 1 and 2...
September 8, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28923409/recent-advances-in-the-chemical-synthesis-of-sugar-nucleotides
#3
Sanaz Ahmadipour, Gavin J Miller
No abstract text is available yet for this article.
September 1, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28881237/synthesis-of-a-series-of-new-glycoclusters-and-the-evaluation-of-their-anti-adhesion-activities
#4
Xiaorong Zhang, Aqin Liu, Zhihui Zhao, Zhongjun Li, Qing Li
According to our early researches, some glycoclusters having glucose, mannose, cellose and lactose residues showed good anti-adhesion activity of leukocytes to endothelial cells and exerted anti-inflammatory effects. Based on these results and combination principles of drugs, a series of new glycoclusters modifying with potentially anti-oxidant activity pharmacophores have been synthesized, and their anti-adhesion activities were assessed by static state cell-based adhesion assay. The results showed that some modified glycoclusters displayed better activities than their leading compound...
September 1, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28910600/an-acceptor-analogue-of-%C3%AE-1-4-galactosyltransferase-substrate-inhibitor-or-both
#5
Jingqian Jiang, Gerd K Wagner
Many glycosyltransferase inhibitors in the literature are structurally derived from the donor or acceptor substrate of the respective enzyme. A representative example is 2-naphthyl β-d-GlcNAc, a synthetic GlcNAc glycoside that has been reported as a galactosyltransferase inhibitor. This GlcNAc derivative is attractive as a chemical tool compound for biological and biochemical studies because of its reported potency as an inhibitor, and its short and straightforward synthesis from readily available starting materials...
August 31, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28869819/rational-optimization-of-the-mannoside-building-block-for-automated-electrochemical-assembly-of-the-core-trisaccharide-of-gpi-anchor-oligosaccharides
#6
Sujit Manmode, Takumi Sato, Norihiko Sasaki, Ikumi Notsu, Shuichi Hayase, Toshiki Nokami, Toshiyuki Itoh
We have developed a carbohydrate building block of mannosides based on DFT calculations, electrochemical analysis, and automated solution-phase synthesis. The optimized building block in hand was used to prepare the core trisaccharide of GPI anchor oligosaccharides.
August 25, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28866079/alternate-synthesis-to-d-glycero-%C3%AE-d-manno-heptose-1-7-biphosphate
#7
Janelle Sauvageau, Milan Bhasin, Cynthia X Guo, Itunuoluwa A Adekoya, Scott D Gray-Owen, Stefan Oscarson, Lorenzo Guazzelli, Andrew Cox
d-glycero-β-d-manno-heptose 1,7-biphosphate (HBP) is an enzymatic intermediate in the biosynthesis of the heptose component of lipopolysaccharide (LPS), and was recently revealed to be a pathogen-associated molecular pattern (PAMP) that allows detection of Gram-negative bacteria by the mammalian immune system. Cellular detection of HBP depends upon its stimulation of a cascade that leads to the phosphorylation and assembly of the TRAF-interacting with forkhead-associated domain protein A (TIFA), which activates the transcription factor NF-κB...
August 24, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28851488/membrane-enclosed-multienzyme-meme-synthesis-of-2-7-anhydro-sialic-acid-derivatives
#8
Marie Monestier, Dimitrios Latousakis, Andrew Bell, Sandra Tribolo, Louise E Tailford, Ian J Colquhoun, Gwenaelle Le Gall, Hai Yu, Xi Chen, Martin Rejzek, Simone Dedola, Robert A Field, Nathalie Juge
Naturally occurring 2,7-anhydro-alpha-N-acetylneuraminic acid (2,7-anhydro-Neu5Ac) is a transglycosylation product of bacterial intramolecular trans-sialidases (IT-sialidases). A facile one-pot two-enzyme approach has been established for the synthesis of 2,7-anhydro-sialic acid derivatives including those containing different sialic acid forms such as Neu5Ac and N-glycolylneuraminic acid (Neu5Gc). The approach is based on the use of Ruminoccocus gnavus IT-sialidase for the release of 2,7-anhydro-sialic acid from glycoproteins, and the conversion of free sialic acid by a sialic acid aldolase...
August 19, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28858610/synthesis-of-a-model-trisaccharide-for-studying-the-interplay-between-the-anti-%C3%AE-gal-antibody-and-the-trans-sialidase-reactions-in-trypanosoma-cruzi
#9
M Eugenia Giorgi, Rosana Lopez, Rosalia Agusti, Carla Marino, Rosa M de Lederkremer
Trypanosoma cruzi, the etiologic agent of Chagas disease, is covered by a dense glycocalix mainly composed by glycoproteins called mucins which are also the acceptors of sialic acid in a reaction catalyzed by a trans-sialidase (TcTS). Sialylation of trypomastigote mucins protects the parasite from lysis by the anti α-Galp antibodies from serum. The TcTS is essential for the infection process since T. cruzi is unable to biosynthesize sialic acid. The enzyme specifically transfers it from a terminal β-d-Galp unit in the host glycoconjugate to terminal β-d-Galp units in the parasite mucins to construct the d-NeuNAc(α2→3)β-d-Galp motif...
August 18, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28837839/genetic-and-structural-elucidation-of-capsular-polysaccharides-from-streptococcus-pneumoniae-serotype-23a-and-23b-and-comparison-to-serotype-23f
#10
Neil Ravenscroft, Aneesa Omar, Jason Hlozek, Cesarina Edmonds-Smith, Rainer Follador, Fabio Serventi, Gerd Lipowsky, Michelle M Kuttel, Paola Cescutti, Amirreza Faridmoayer
Streptococcus pneumoniae is a globally important encapsulated human pathogen with approximately 100 different serotypes recognized. Serogroup 23 consists of serotype 23F, present in licensed vaccines, and emerging serotypes 23A and 23B. Here, we report the previously unknown structures of the pneumococcal capsular polysaccharides serotype 23A and 23B determined using genetic analysis, NMR spectroscopy, composition and linkage analysis and Smith degradation (of polysaccharide 23A). The structure of the serotype 23A capsular polysaccharide is: →4)-β-D-Glcp-(1→3)-[[α-L-Rhap-(1→2)]-[Gro-(2→P→3)]-β-D-Galp-(1→4)]-β-L-Rhap-(1→...
August 18, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28822279/chemical-synthesis-of-guanosine-diphosphate-mannuronic-acid-gdp-mana-and-its-c-4-o-methyl-and-c-4-deoxy-congeners
#11
Qingju Zhang, P Lynne Howell, Herman S Overkleeft, Dmitri V Filippov, Gijsbert A van der Marel, Jeroen D C Codée
Described is the first synthesis of guanosine diphosphate mannuronic acid (GDP-ManA), the sugar donor used by algae and bacteria for the production of alginate, an anionic polysaccharide composed of β-d-mannuronic acid (ManA) and α-l-guluronic acid (GulA). Understanding the biosynthesis of these polyanionic polysaccharides on the molecular level, opens up avenues to use and modulate the biosynthesis machinery for biotechnological and therapeutic applications. The synthesis reported here delivers multi-milligram amounts of the GDP-ManA donor that can be used to study the polymerase (Alg8 in Pseudomonas aeruginosa) that generates the poly-ManA chain...
August 11, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28822278/a-carbon-tetrachloride-free-synthesis-of-n-phenyltrifluoroacetimidoyl-chloride
#12
Dylan G M Smith, Spencer J Williams
N-Phenyltrifluoroacetimidoyl chloride (PTFAI-Cl) is a reagent widely used for the preparation of glycosyl N-phenyltrifluoroacetimidates. However, the most commonly applied method requires carbon tetrachloride, a hepatotoxic reagent that has been phased out under the Montreal Protocol. We report a new synthesis of N-phenyltrifluoroacetimidoyl chloride (PTFAI-Cl) using dichlorotriphenylphosphane and triethylamine.
August 10, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28917089/the-trehalose-specific-transporter-lpqy-sugabc-is-required-for-antimicrobial-and-anti-biofilm-activity-of-trehalose-analogues-in-mycobacterium-smegmatis
#13
Jeffrey M Wolber, Bailey L Urbanek, Lisa M Meints, Brent F Piligian, Irene C Lopez-Casillas, Kailey M Zochowski, Peter J Woodruff, Benjamin M Swarts
Mycobacteria, including the bacterial pathogen that causes human tuberculosis, possess distinctive pathways for synthesizing and utilizing the non-mammalian disaccharide trehalose. Trehalose metabolism is essential for mycobacterial viability and has been linked to in vitro biofilm formation, which may bear relevance to in vivo drug tolerance. Previous research has shown that some trehalose analogues bearing modifications at the 6-position inhibit growth of various mycobacterial species. In this work, 2-, 5-, and 6-position-modified trehalose analogues were synthesized using our previously reported one-step chemoenzymatic method and shown to inhibit growth and biofilm formation in the two-to three-digit micromolar range in Mycobacterium smegmatis...
August 9, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28818771/one-pot-synthesis-of-oxazolidine-2-thione-and-thiozolidine-2-thione-from-sugar-azido-alcohols
#14
Kunj B Mishra, Anand K Agrahari, Vinod K Tiwari
A controlled and facile synthesis of various glycosyl 1,3-oxazolidine-2-thiones and 1,3- thiozolidine-2-thiones has been accomplished from corresponding sugar azido alcohols utilizing Staudinger reaction (PPh3 and CS2) via isothiocynate route. A series of reactions were performed to investigate the effects of CS2 and PPh3 on the selectivity of product formed. The excessive addition of CS2 with PPh3(1.2 equiv) afforded oxazolidine-2-thione alone, while the solitary addition of PPh3 for 30 min followed by addition of CS2 to the reaction mixture resulted both the products in different ratios, which were successfully isolated using column chromatography (SiO2)...
August 4, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28760417/cellodextrin-phosphorylase-from-ruminiclostridium-thermocellum-x-ray-crystal-structure-and-substrate-specificity-analysis
#15
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 2.4.1.49) 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
https://www.readbyqxmd.com/read/28669498/imaging-of-protein-specific-glycosylation-by-glycan-metabolic-tagging-and-in-situ-proximity-ligation
#16
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/28800498/erylosides-f8-v1-v3-and-w-w2-new-triterpene-oligoglycosides-from-the-carribean-sponge-erylus-goffrilleri
#17
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...
September 8, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28800497/glycoconjugate-probes-containing-a-core-fucosylated-n-glycan-trisaccharide-for-fucose-lectin-identification-and-purification
#18
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...
September 8, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28783569/pyruvylated-cell-wall-glycopolymers-of-promicromonospora-citrea-vkm-a%C3%A2-665-t-and-promicromonospora-sp-vkm-a%C3%A2-1028
#19
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...
September 8, 2017: Carbohydrate Research
https://www.readbyqxmd.com/read/28780317/enzymatic-synthesis-of-ribo-and-2-deoxyribonucleosides-from-glycofuranosyl-phosphates-an-approach-to-facilitate-isotopic-labeling
#20
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...
September 8, 2017: Carbohydrate Research
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