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December 2016: Glycobiology
Jerrard M Hayes, Mark R Wormald, Pauline M Rudd, Gavin P Davey
Therapeutic antibodies hold great promise for the treatment of cancer and autoimmune diseases, and developments in antibody-drug conjugates and bispecific antibodies continue to enhance treatment options for patients. Immunoglobulin (Ig) G antibodies are proteins with complex modifications, which have a significant impact on their function. The most important of these modifications is glycosylation, the addition of conserved glycans to the antibody Fc region, which is critical for its interaction with the immune system and induction of effector activities such as antibody-dependent cell cytotoxicity, complement activation and phagocytosis...
2016: Journal of Inflammation Research
Cédric Przybylski, Juan M Benito, Véronique Bonnet, Carmen Ortiz Mellet, José M García Fernández
Polycationic carbohydrates represent an attractive class of biomolecules for several applications and particularly as non viral gene delivery vectors. In this case, the establishment of structure-biological activity relationship requires sensitive and accurate characterization tools to both control and achieve fine structural deciphering. Electrospray-tandem mass spectrometry (ESI-MS/MS) appears as a suitable approach to address these questions. In the study herein, we have investigated the usefulness of electron transfer dissociation (ETD) to get structural data about five polycationic carbohydrates demonstrated as promising gene delivery agents...
December 15, 2016: Analytica Chimica Acta
Chao Li, Lai-Xi Wang
Recent advances in glycobiology have implicated essential roles of oligosaccharides and glycoconjugates in many important biological recognition processes, including intracellular signaling, cell adhesion, cell differentiation, cancer progression, host-pathogen interactions, and immune responses. A detailed understanding of the biological functions, as well as the development of carbohydrate-based therapeutics, often requires structurally well-defined oligosaccharides and glycoconjugates, which are usually difficult to isolate in pure form from natural sources...
2016: Advances in Carbohydrate Chemistry and Biochemistry
N Chen, J Xie
The importance of oligosaccharides and their conjugates in various biological and pathological processes has stimulated growing interest in the development of (neo)glycoconjugates. Thanks to its high nucleophilicity, hydroxylamine has been employed as a powerful chemoselective ligation tool. Great effort has been focused on carbohydrates bearing aminooxy or N-hydroxy amino groups for organic synthesis, glycobiology and drug discovery. This review provides an overview of N-O linked carbohydrates and glycoconjugates, focusing particularly on the synthetic methodologies and chemical and physicochemical properties as well as biological and medical applications of N-glycosyl and O-glycosyl hydroxylamines, N-hydroxy amino and O-amino sugar as well as sugar aminooxy acid derivatives...
November 1, 2016: Organic & Biomolecular Chemistry
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No abstract text is available yet for this article.
October 31, 2016: Glycobiology
Shiyue Zhou, Xue Dong, Lucas Veillon, Yifan Huang, Yehia Mechref
The biosynthesis of glycans is a template-free process; hence compositionally identical glycans may contain highly heterogeneous structures. Meanwhile, the functions of glycans in biological processes are significantly influenced by the glycan structure. Structural elucidation of glycans is an essential component of glycobiology. Although NMR is considered the most powerful approach for structural glycan studies, it suffers from low sensitivity and requires highly purified glycans. Although mass spectrometry (MS)-based methods have been applied in numerous glycan structure studies, there are challenges in preserving glycan structure during ionization...
October 28, 2016: Analytical and Bioanalytical Chemistry
Gour Chand Daskhan, Carlo Pifferi, Olivier Renaudet
The synthesis of heteroglycoclusters (hGCs) is being subjected to rising interest, owing to their potential applications in glycobiology. In this paper, we report an efficient and straightforward convergent protocol based on orthogonal chemoselective ligations to prepare structurally well-defined cyclopeptide-based homo- and heterovalent glycoconjugates displaying 5-N-acetyl-neuraminic acid (Neu5Ac), galactose (Gal), and/or N-acetyl glucosamine (GlcNAc). We first used copper-catalyzed azide-alkyne cycloaddition and/or thiol-ene coupling to conjugate propargylated α-sialic acid 3, β-GlcNAc thiol 5, and β-Gal thiol 6 onto cyclopeptide scaffolds 7-9 to prepare tetravalent homoglycoclusters (10-12) and hGCs (13-14) with 2:2 combinations of sugars...
October 2016: ChemistryOpen
Rituparna Das, Balaram Mukhopadhyay
The development of glycobiology relies on the sources of particular oligosaccharides in their purest forms. As the isolation of the oligosaccharide structures from natural sources is not a reliable option for providing samples with homogeneity, chemical means become pertinent. The growing demand for diverse oligosaccharide structures has prompted the advancement of chemical strategies to stitch sugar molecules with precise stereo- and regioselectivity through the formation of glycosidic bonds. This Review will focus on the key developments towards chemical O-glycosylations in the current century...
October 2016: ChemistryOpen
Oliver R Baudendistel, Daniel E Wieland, Magnus S Schmidt, Valentin Wittmann
Ligation reactions at the anomeric center of carbohydrates have gained increasing importance in the field of glycobiology. Oxyamines are frequently used in labeling, immobilization, and bioconjugation of reducing carbohydrates. Herein, we present a systematic investigation of these ligation reactions under aqueous conditions. A series of four unprotected monosaccharides (glucose, N-acetylglucosamine, mannose, and 2-deoxyglucose) and one disaccharide (N,N'-diacetylchitobiose) was reacted with three primary and one secondary oxyamine...
November 21, 2016: Chemistry: a European Journal
Nathan J Hare, Ling Y Lee, Ian Loke, Warwick J Britton, Bernadette M Saunders, Morten Thaysen-Andersen
Tuberculosis (TB) remains a prevalent and lethal infectious disease. The glycobiology associated with Mycobacterium tuberculosis infection of front-line alveolar macrophages is still unresolved. Herein, we investigated the regulation of protein N-glycosylation in human macrophages and their secreted microparticles (MPs) used for intercellular communication upon M. tb infection. LC-MS/MS-based proteomics and glycomics were performed to monitor the regulation of glycosylation enzymes and receptors and the N-glycome in in vitro-differentiated macrophages and in isolated MPs upon M...
October 19, 2016: Journal of Proteome Research
Frederique Lisacek, Julien Mariethoz, Davide Alocci, Pauline M Rudd, Jodie L Abrahams, Matthew P Campbell, Nicolle H Packer, Jonas Ståhle, Göran Widmalm, Elaine Mullen, Barbara Adamczyk, Miguel A Rojas-Macias, Chunsheng Jin, Niclas G Karlsson
The access to biodatabases for glycomics and glycoproteomics has proven to be essential for current glycobiological research. This chapter presents available databases that are devoted to different aspects of glycobioinformatics. This includes oligosaccharide sequence databases, experimental databases, 3D structure databases (of both glycans and glycorelated proteins) and association of glycans with tissue, disease, and proteins. Specific search protocols are also provided using tools associated with experimental databases for converting primary glycoanalytical data to glycan structural information...
2017: Methods in Molecular Biology
Jorin Hoogenboom, Nathalja Berghuis, Dario Cramer, Rene Geurts, Han Zuilhof, Tom Wennekes
BACKGROUND: Carbohydrates, also called glycans, play a crucial but not fully understood role in plant health and development. The non-template driven formation of glycans makes it impossible to image them in vivo with genetically encoded fluorescent tags and related molecular biology approaches. A solution to this problem is the use of tailor-made glycan analogs that are metabolically incorporated by the plant into its glycans. These metabolically incorporated probes can be visualized, but techniques documented so far use toxic copper-catalyzed labeling...
October 10, 2016: BMC Plant Biology
Monika S Doblin, Debra Mohnen, Antony Bacic
No abstract text is available yet for this article.
September 2016: Glycobiology
Wan-Ling Ho, Wen-Ming Hsu, Min-Chuan Huang, Kenji Kadomatsu, Akira Nakagawara
Glycosylation is the most complex post-translational modification of proteins. Altered glycans on the tumor- and host-cell surface and in the tumor microenvironment have been identified to mediate critical events in cancer pathogenesis and progression. Tumor-associated glycan changes comprise increased branching of N-glycans, higher density of O-glycans, generation of truncated versions of normal counterparts, and generation of unusual forms of terminal structures arising from sialylation and fucosylation. The functional role of tumor-associated glycans (Tn, sTn, T, and sLe(a/x)) is dependent on the interaction with lectins...
September 29, 2016: Journal of Hematology & Oncology
Moacyr J B M Rêgo, Antônio F Silva Filho, Ana P V Sobral, Eduardo I C Beltrão
The formation of new and functional structural components of several organs, such as parotid glands, can be influenced by the glycocode. This study analyzed the glycobiology of parotid salivary gland tissue during fetal development using specific biochemical probes (lectins and antibodies). Eleven parotid gland samples from human fetuses were obtained from spontaneous abortions at 14-28 weeks of gestation, and tissue sections were analyzed for lectin histochemistry and immunohistochemistry. From the 18th to 26th week, Canavalia ensiformis agglutinin, wheat germ agglutinin, Ulex europaeus agglutinin-I, peanut agglutinin, Sambucus nigra agglutinin, and Vicia villosa agglutinin lectin staining were predominantly observed in the apical and/or basement membranes of the ducts and tubulo-acinar units...
2016: Journal of Oral Science
Bruce A Baggenstoss, Edward N Harris, Jennifer L Washburn, Andria P Medina, Long Nguyen, Paul H Weigel
Hyaluronan synthases (HAS) normally make large (>MDa) hyaluronan (HA) products. Smaller HA fragments (e.g. 100-400 kDa) produced in vivo are associated with inflammation and cell signaling by HA receptors that bind small, but not large, HA. Although HA fragments can arise from breakdown by hyaluronidases, HAS might also be regulated directly to synthesize small HA. Here we examined the Streptococcus equisimilis HAS (SeHAS) C-terminus, which contains a tandem B-X7-B motif (K(398)-X7-R(406)-X7-K(414)), by testing the effects of 27 site-specific scanning mutations and 7 C-terminal truncations on HA synthesis activity and weight-average mass...
August 24, 2016: Glycobiology
Pierre-André Gilormini, Cédric Lion, Maxence Noel, Marie-Ange Krzewinski-Recchi, Anne Harduin-Lepers, Yann Guérardel, Christophe Biot
Natural and synthetically modified CMP-activated sialic acids are essential research tools in the field of glycobiology: among other applications, they can be used to probe glycans, detect sialylation defects at the cell surface, or carry out detailed studies of sialyltransferase activities. However, these chemical tools are notoriously unstable because of hydrolytic decomposition, and are very time-consuming and costly to obtain. They are nigh impossible to store with satisfactory purity, and their preparation requires multiple laborious purification steps that usually lead to heavy product loss...
August 19, 2016: Glycobiology
Mohamed I Hassan, Benjamin R Lundgren, Michael Chaumun, Dennis M Whitfield, Brady Clark, Ian C Schoenhofen, Christopher N Boddy
Legionaminic acid, Leg5,7Ac2 , a nonulosonic acid like 5-acetamido neuraminic acid (Neu5Ac, sialic acid), is found in cell surface glycoconjugates of bacteria including the pathogens Campylobacter jejuni, Acinetobacter baumanii and Legionella pneumophila. The presence of Leg5,7Ac2 has been correlated with virulence in humans by mechanisms that likely involve subversion of the host's immune system or interactions with host cell surfaces due to its similarity to Neu5Ac. Investigation into its role in bacterial physiology and pathogenicity is limited as there are no effective sources of it...
September 19, 2016: Angewandte Chemie
Guangyan Qing, Xiuling Li, Peng Xiong, Cheng Chen, Mimi Zhan, Xinmiao Liang, Taolei Sun
Glycoproteomics identifies and catalogs protein glycosylation and explores its impact on protein conformations and biofunctions. However, these studies are restricted by the bottleneck to enrich low-abundance glycopeptides from complex biosamples and the difficulties in analyzing glycan structures by mass spectrometry. Here, we report dipeptide as a simple but promising carbohydrate binding platform to tackle these problems. We build a hydropathy-index-based strategy for sequence optimization and screen out three optimal dipeptide sequences from 54 types of dipeptides...
August 31, 2016: ACS Applied Materials & Interfaces
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