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Julie Y Zhou, Douglas M Oswald, Kelsey D Oliva, Lori S C Kreisman, Brian A Cobb
Carbohydrates, or glycans, are as integral to biology as nucleic acids and proteins. In immunology, glycans are well known to drive diverse functions ranging from glycosaminoglycan-mediated chemokine presentation and selectin-dependent leukocyte trafficking to the discrimination of self and non-self through the recognition of sialic acids by Siglec (sialic acid-binding Ig-like lectin) receptors. In recent years, a number of key immunological discoveries are driving a renewed and burgeoning appreciation for the importance of glycans...
May 11, 2018: Trends in Immunology
Douglas M Oswald, Brian A Cobb
The glycobiology of the immune response is a topic that has garnered increased attention due to a number of key discoveries surrounding IgG function, the specificity of some broadly neutralizing anti-HIV antibodies, cancer immunoregulation by galectin molecules and others. This review is the opening article in a Special Edition of Cellular Immunology focused on glycoimmunology, and has the goal of setting the context for these articles by providing a mini-review of how glycans impact immunity. We also focus on some of the technological and methodological advances in the field of glycobiology that are being deployed to lower the barrier of entry into the glycosciences, and to more fully interrogate the glycome and its function...
April 25, 2018: Cellular Immunology
Alonso Pardo-Vargas, Martina Delbianco, Peter H Seeberger
Access to complex carbohydrates remains a limiting factor for the development of the glycosciences. Automated glycan assembly (AGA) has accelerated and simplified the synthetic process and, with the first commercially available instrument and building blocks, glycan synthesis can now be practiced by any chemist. All classes of glycans, including sulfated or sialylated carbohydrates and polysaccharides as long as 50mers are now accessible owing to optimized reaction conditions and new methodologies. These synthetic glycans have helped to understand many biological functions and to advance diagnostic and vaccine development...
April 28, 2018: Current Opinion in Chemical Biology
Jessica Poole, Christopher J Day, Mark von Itzstein, James C Paton, Michael P Jennings
Many important interactions between bacterial pathogens and their hosts are highly specific binding events that involve host or pathogen carbohydrate structures (glycans). Glycan interactions can mediate adhesion, invasion and immune evasion and can act as receptors for toxins. Several bacterial pathogens can also enzymatically alter host glycans to reveal binding targets, degrade the host cell glycans or alter the function of host glycoproteins. In recent years, high-throughput screening technologies, such as lectin, glycan and mucin microarrays, have transformed the field by identifying new bacterial-host glycointeractions, which are crucial for colonization, persistence and disease...
April 19, 2018: Nature Reviews. Microbiology
Elena Solovieva, Toshihide Shikanai, Noriaki Fujita, Hisashi Narimatsu
BACKGROUND: Inherited mutations in glyco-related genes can affect the biosynthesis and degradation of glycans and result in severe genetic diseases and disorders. The Glyco-Disease Genes Database (GDGDB), which provides information about these diseases and disorders as well as their causative genes, has been developed by the Research Center for Medical Glycoscience (RCMG) and released in April 2010. GDGDB currently provides information on about 80 genetic diseases and disorders caused by single-gene mutations in glyco-related genes...
April 18, 2018: Journal of Biomedical Semantics
Ana Ardá, Jesús Jiménez-Barbero
Carbohydrates (glycans, saccharides, sugars) are everywhere. In fact, glycan-protein interactions are involved in many essential processes of life and disease. The understanding of the key structural details at the atomic and molecular level is of paramount importance to effectively design molecules for therapeutic purposes. Different approximations may be employed to decipher these molecular recognition processes with high resolution. Advances in cryo-electron microscopy are providing exquisite details on different biological mechanisms involving sugars, while better and better protocols for structural refinement in the application of X-ray methods for protein-sugar complexes and glycoproteins are also permitting fantastic advances in the glycoscience arena...
April 17, 2018: Chemical Communications: Chem Comm
Ivan Yu Chernyshov, Philip V Toukach
Motivation: Glycans and glycoconjugates are usually recorded in dedicated databases in residue-based notations. Only a few of them can be converted into chemical (atom-based) formats highly demanded in conformational and biochemical studies. In this work, we present a tool for translation from a residue-based glycan notation to SMILES. Results: The REStLESS algorithm for translation from the CSDB Linear notation to SMILES was developed. REStLESS stands for ResiduEs as Smiles and LinkagEs as SmartS, where SMARTS reaction expressions are used to merge pre-encoded residues into a molecule...
March 14, 2018: Bioinformatics
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-François Nierengarten, Jérémy P Schneider, Thi Minh Nguyet Trinh, Antoine Joosten, Michel Holler, Mathieu L Lepage, Anne Bodlenner, M Isabel García-Moreno, Carmen Ortiz Mellet, Philippe Compain
The multivalent effect in glycosidase inhibition is a new topic in glycoscience that has emerged a 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...
February 16, 2018: 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...
March 15, 2018: 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 the study of protein•carbohydrate complexes. However, experimental obstacles and data analysis are preventing faster integration of AMS methods into the glycoscience field. Here we show how analysis of direct electrospray ionization mass spectrometry (ESI-MS) AMS data can be simplified for screening purposes, even for complex AMS spectra. METHODS: A direct ESI-MS assay was tested in this study and binding data for the galectin-3C•lactose complex were analyzed using a comprehensive and simplified data analysis approach...
October 30, 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
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