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Grace Lu, Cassandra L Crihfield, Srikanth Gattu, Lindsay M Veltri, Lisa A Holland
Capillary electrophoresis has emerged as a powerful approach for carbohydrate analyses since 2014. The method provides high resolution capable of separating carbohydrates by charge-to-size ratio. Principle applications are heavily focused on N-glycans, which are highly relevant to biological therapeutics and biomarker research. Advances in techniques used for N-glycan structural identification include migration time indexing and exoglycosidase and lectin profiling, as well as mass spectrometry. Capillary electrophoresis methods have been developed that are capable of separating glycans with the same monosaccharide sequence but different positional isomers, as well as determining whether monosaccharides composing a glycan are alpha or beta linked...
March 12, 2018: Chemical Reviews
Vivek Poonthiyil, Thisbe K Lindhorst, Vladimir B Golovko, Antony J Fairbanks
Glycoscience, despite its myriad of challenges, promises to unravel the causes of, potential new detection methods for, and novel therapeutic strategies against, many disease states. In the last two decades, glyco-gold nanoparticles have emerged as one of several potential new tools for glycoscientists. Glyco-gold nanoparticles consist of the unique structural combination of a gold nanoparticle core and an outer-shell comprising multivalent presentation of carbohydrates. The combination of the distinctive physicochemical properties of the gold core and the biological function/activity of the carbohydrates makes glyco-gold nanoparticles a valuable tool in glycoscience...
2018: Beilstein Journal of Organic Chemistry
Jean-Francois Nierengarten, Jérémy P Schneider, Thi Minh Nguyet Trinh, Antoine Joosten, Michel Holler, Mathieu L Lepage, Anne Bodlenner, Isabel Garcia-Moreno, Carmen Ortiz Mellet, Philippe Compain
The multivalent effect in glycosidase inhibition is a new topic in glycoscience that has emerged few years ago with the discovery of neoglycoclusters displaying strong binding enhancements over the corresponding monovalent inhibitor. Iminosugar-fullerene conjugates with high valencies have been prepared from iminosugar-terminated dendrons and a clickable fullerene hexa-adduct scaffold. The simultaneous grafting of twelve dendrons allows for a very fast dendritic growth thus limiting the number of synthetic steps required to prepare compounds with a high number of peripheral units...
December 27, 2017: Chemistry: a European Journal
Keith J Stine
There is a growing interest in using a range of porous materials to meet research needs in carbohydrate chemistry and glycoscience in general. Among the applications of porous materials reviewed in this chapter, enrichment of glycans from biological samples prior to separation and analysis by mass spectrometry is a major emphasis. Porous materials offer high surface area, adjustable pore sizes, and tunable surface chemistry for interacting with glycans, by boronate affinity, hydrophilic interactions, molecular imprinting, and polar interactions...
2017: Advances in Carbohydrate Chemistry and Biochemistry
Brian S Hamilton, Joshua D Wilson, Marina A Shumakovich, Adam C Fisher, James C Brooks, Alyssa Pontes, Radnaa Naran, Christian Heiss, Chao Gao, Robert Kardish, Jamie Heimburg-Molinaro, Parastoo Azadi, Richard D Cummings, Judith H Merritt, Matthew P DeLisa
Synthesis of homogenous glycans in quantitative yields represents a major bottleneck to the production of molecular tools for glycoscience, such as glycan microarrays, affinity resins, and reference standards. Here, we describe a combined biological/enzymatic synthesis that is capable of efficiently converting microbially-derived precursor oligosaccharides into structurally uniform human-type N-glycans. Unlike starting material obtained by chemical synthesis or direct isolation from natural sources, which can be time consuming and costly to generate, our approach involves precursors derived from renewable sources including wild-type Saccharomyces cerevisiae glycoproteins and lipid-linked oligosaccharides from glycoengineered Escherichia coli...
November 21, 2017: Scientific Reports
Roman R Kapaev, Philip V Toukach
Motivation: Carbohydrates play crucial roles in various biochemical processes and are useful for developing drugs and vaccines. However, in case of carbohydrates, the primary structure elucidation is usually a sophisticated task. Therefore, they remain the least structurally characterized class of biomolecules, and it hampers the progress in glycochemistry and glycobiology. Creating a usable instrument designed to assist researchers in natural carbohydrate structure determination would advance glycochemistry in biomedical and pharmaceutical applications...
October 28, 2017: Bioinformatics
Baptiste Schindler, Loïc Barnes, Gina Renois, Christopher Gray, Stéphane Chambert, Sébastien Fort, Sabine Flitsch, Claire Loison, Abdul-Rahman Allouche, Isabelle Compagnon
Deciphering the carbohydrate alphabet is problematic due to its unique complexity among biomolecules. Strikingly, routine sequencing technologies-which are available for proteins and DNA and have revolutionised biology-do not exist for carbohydrates. This lack of structural tools is identified as a crucial bottleneck, limiting the full development of glycosciences and their considerable potential impact for the society. In this context, establishing generic carbohydrate sequencing methods is both a major scientific challenge and a strategic priority...
October 17, 2017: Nature Communications
(no author information available yet)
No abstract text is available yet for this article.
September 7, 2017: Glycobiology
Marc R Hayes, Jörg Pietruszka
The many advances in glycoscience have more and more brought to light the crucial role of glycosides and glycoconjugates in biological processes. Their major influence on the functionality and stability of peptides, cell recognition, health and immunity and many other processes throughout biology has increased the demand for simple synthetic methods allowing the defined syntheses of target glycosides. Additional interest in glycoside synthesis has arisen with the prospect of producing sustainable materials from these abundant polymers...
August 30, 2017: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Ahmad A Zeidan, Vera Kuzina Poulsen, Thomas Janzen, Patrizia Buldo, Patrick M F Derkx, Gunnar Øregaard, Ana Rute Neves
The ability to produce polysaccharides with diverse biological functions is widespread in bacteria. In lactic acid bacteria (LAB), production of polysaccharides has long been associated with the technological, functional and health-promoting benefits of these microorganisms. In particular, the capsular polysaccharides and exopolysaccharides have been implicated in modulation of the rheological properties of fermented products. For this reason, screening and selection of exocellular polysaccharide-producing LAB has been extensively carried out by academia and industry...
August 1, 2017: FEMS Microbiology Reviews
Marko Haramija, Jasna Peter-Katalinić
RATIONALE: Affinity mass spectrometry (AMS) is an emerging tool in the field of study of protein-carbohydrate complexes. However, experimental obstacles and data analysis is preventing faster integration of AMS methods in the field of glycosciences. Here we show how analysis of direct ESI-MS AMS data can be simplified for screening purposes, even for complex AMS spectra. METHODS: Direct ESI-MS assay was tested in this study, and binding data for the galectin-3C•lactose complex were analyzed using comprehensive and simplified data analysis approach...
August 14, 2017: Rapid Communications in Mass Spectrometry: RCM
Xiang Fei, Megan E Zavorka, Guillaume Malik, Christopher M Connelly, Richard G MacDonald, David B Berkowitz
A generalized strategy is presented for the rapid assembly of a set of bivalent ligands with a variety of linking functionalities from a common monomer. Herein, an array of phosphatase-inert mannose-6-phosphonate-presenting ligands for the cation-independent-mannose 6-phosphate receptor (CI-MPR) is constructed. Receptor binding affinity varies with linking functionality-the simple amide and 1,5-triazole(tetrazole) being preferred over the 1,4-triazole. This approach is expected to find application across chemical biology, particularly in glycoscience, wherein multivalency often governs molecular recognition...
July 28, 2017: Organic Letters
Kenichi G N Suzuki, Hiromune Ando, Naoko Komura, Takahiro K Fujiwara, Makoto Kiso, Akihiro Kusumi
Gangliosides are involved in a variety of biological roles and are a component of lipid rafts found in cell plasma membranes (PMs). Gangliosides are especially abundant in neuronal PMs and are essential to their physiological functions. However, the dynamic behaviors of gangliosides have not been investigated in living cells due to a lack of fluorescent probes that behave like their parental molecules. We have recently developed, using an entirely chemical method, four new ganglioside probes (GM1, GM2, GM3, and GD1b) that act similarly to their parental molecules in terms of raft partitioning and binding affinity...
October 2017: Biochimica et Biophysica Acta
Saeideh Shamsi Kazem Abadi, Michael Tran, Anuj K Yadav, Pal John Pal Adabala, Saswati Chakladar, Andrew J Bennet
The design of covalent inhibitors in glycoscience research is important for the development of chemical biology probes. Here we report the synthesis of a new carbocyclic mechanism-based covalent inhibitor of an α-glucosidase. The enzyme efficiently catalyzes its alkylation via either an allylic cation or a cationic transition state. We show this allylic covalent inhibitor has different catalytic proficiencies for pseudoglycosylation and deglycosylation. Such inhibitors have the potential to be useful chemical biology tools...
August 9, 2017: Journal of the American Chemical Society
Hiroshi Manya, Tamao Endo
BACKGROUND: O-mannosyl glycans have been found in a limited number of glycoproteins of the brain, nerves, and skeletal muscles, particularly in α-dystroglycan (α-DG). Defects in O-mannosyl glycan on α-DG are the primary cause of a group of congenital muscular dystrophies, which are collectively termed α-dystroglycanopathy. Recent studies have revealed various O-mannosyl glycan structures, which can be classified as core M1, core M2, and core M3 glycans. Although many dystroglycanopathy genes are involved in core M3 processing, the structure and biosynthesis of core M3 glycan remains only partially understood...
October 2017: Biochimica et Biophysica Acta
Kyoka Hoshi, Yuka Matsumoto, Hiromi Ito, Kiyoshi Saito, Takashi Honda, Yoshiki Yamaguchi, Yasuhiro Hashimoto
BACKGROUND: Cerebrospinal fluid (CSF) is sequestered from blood by the blood-brain barrier and directly communicates with brain parenchymal interstitial fluid, leading to contain specific biomarkers of neurological diseases. SCOPE OF REVIEW: CSF contains glycan isoforms of transferrin (Tf): one appears to be derived from the brain and the other from blood. MAJOR CONCLUSIONS: CSF contains two glycan-isoforms; brain-type Tf and serum-type Tf...
October 2017: Biochimica et Biophysica Acta
Yamin Abdouni, Gokhan Yilmaz, C Remzi Becer
Glycopolymers are synthetic-carbohydrate-containing materials capable of interacting and binding to specific targeting lectins, which are crucially important in many biologically active processes. Over the last decade, advances in synthetic chemistry and polymerization techniques have enabled the development of sequence and architecturally controlled glycopolymers for different types of bioapplications, such as drug delivery and release purposes, gene therapy, lectin-based biosensors, and much more in the future...
July 10, 2017: Macromolecular Rapid Communications
Serge Pérez, Daniele de Sanctis
Synchrotron radiation is the most versatile way to explore biological materials in different states: monocrystalline, polycrystalline, solution, colloids and multiscale architectures. Steady improvements in instrumentation have made synchrotrons the most flexible intense X-ray source. The wide range of applications of synchrotron radiation is commensurate with the structural diversity and complexity of the molecules and macromolecules that form the collection of substrates investigated by glycoscience. The present review illustrates how synchrotron-based experiments have contributed to our understanding in the field of structural glycobiology...
2017: Beilstein Journal of Organic Chemistry
Vivien Marx
No abstract text is available yet for this article.
June 29, 2017: Nature Methods
Chiara Masellis, Neelam Khanal, Michael Z Kamrath, David E Clemmer, Thomas R Rizzo
The structural characterization of glycans by mass spectrometry is particularly challenging. This is because of the high degree of isomerism in which glycans of the same mass can differ in their stereochemistry, attachment points, and degree of branching. Here we show that the addition of cryogenic vibrational spectroscopy to mass and mobility measurements allows one to uniquely identify and characterize these complex biopolymers. We investigate six disaccharide isomers that differ in their stereochemistry, attachment point of the glycosidic bond, and monosaccharide content, and demonstrate that we can identify each one unambiguously...
October 2017: Journal of the American Society for Mass Spectrometry
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