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Search for "glycans" in Full Text gives 76 result(s) in Beilstein Journal of Organic Chemistry.

Synthesis, docking study and biological evaluation of ᴅ-fructofuranosyl and ᴅ-tagatofuranosyl sulfones as potential inhibitors of the mycobacterial galactan synthesis targeting the galactofuranosyltransferase GlfT2

  • Marek Baráth,
  • Jana Jakubčinová,
  • Zuzana Konyariková,
  • Stanislav Kozmon,
  • Katarína Mikušová and
  • Maroš Bella

Beilstein J. Org. Chem. 2020, 16, 1853–1862, doi:10.3762/bjoc.16.152

Graphical Abstract
  • -factor for the proper synthesis of N-glycans [13]. Subsequently, pioneer structures based on ᴅ-fructofuranose [14], ᴅ-tagatofuranose or ᴅ-psicofuranose [15][16] have been prepared, but their inhibitory activity could not have been tested due to their low stability under standard conditions [16]. Further
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Published 27 Jul 2020

Synthesis of new asparagine-based glycopeptides for future scanning tunneling microscopy investigations

  • Laura Sršan and
  • Thomas Ziegler

Beilstein J. Org. Chem. 2020, 16, 888–894, doi:10.3762/bjoc.16.80

Graphical Abstract
  • example, in anti-HIV therapy, MUC1-based antitumor vaccines, or as antibiotics [12][13][14]. Especially glycans bearing noncanonical amino acids, which can only be introduced into a peptide by organic synthesis, are suitable for cancer therapy since they show better resistance to enzymatic degradation in
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Published 30 Apr 2020

SnCl4-catalyzed solvent-free acetolysis of 2,7-anhydrosialic acid derivatives

  • Kesatebrhan Haile Asressu and
  • Cheng-Chung Wang

Beilstein J. Org. Chem. 2019, 15, 2990–2999, doi:10.3762/bjoc.15.295

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  • University, Hsinchu 300, Taiwan 10.3762/bjoc.15.295 Abstract Sialic acid-containing glycans are found in different sialic acid forms and a variety of glycosidic linkages in biologically active glycoconjugates. Hence, the preparation of suitably protected sialyl building blocks requires high attention in
  • order to access glycans in a pure form. In line with this, various C-5-substituted 2,7-anhydrosialic acid derivatives bearing both electron-donating and -withdrawing protecting groups were synthesized and subjected to different Lewis acid-catalyzed solvent-free ring-opening reactions at room temperature
  • thiosialoside and halide donors. Keywords: acetolysis; acetolysis products; 2,7-anhydrosialic acid; SnCl4; Introduction Sialic acids are the most prevalent monosaccharides that are found at the nonreducing ends of glycans, and they are involved in many biologically important ligand–receptor interactions [1
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Published 23 Dec 2019

Automated glycan assembly of arabinomannan oligosaccharides from Mycobacterium tuberculosis

  • Alonso Pardo-Vargas,
  • Priya Bharate,
  • Martina Delbianco and
  • Peter H. Seeberger

Beilstein J. Org. Chem. 2019, 15, 2936–2940, doi:10.3762/bjoc.15.288

Graphical Abstract
  • lipoarabinomannan (LAM) analogs in urine samples using the Alere lateral flow urine (LF)-LAM assay [13]. However, the low sensitivity of the Alere assay limits its scope. Glycan array screening of more than 100 monoclonal antibodies against more than 60 synthetic glycans related to the mycobacterial cell wall
  • complex glycans [21], including linear and branched oligoarabinofuranosides α-(1,5)- and α-(1,3)- [22] as well as arabinomannose [23][24]. Herein, we describe the AGA of oligosaccharides 4–9 that resemble portions of the MTB AM core structure (Scheme 1). Just three building blocks, namely 1–3, were
  • Mai Hoang for the proofreading of the manuscript. This work used Dr. Bharate’s thesis “Automated Glycan Assembly of Oligomannose Glycans for Sensing Applications” as a source.
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Published 06 Dec 2019

Stereo- and regioselective hydroboration of 1-exo-methylene pyranoses: discovery of aryltriazolylmethyl C-galactopyranosides as selective galectin-1 inhibitors

  • Alexander Dahlqvist,
  • Axel Furevi,
  • Niklas Warlin,
  • Hakon Leffler and
  • Ulf J. Nilsson

Beilstein J. Org. Chem. 2019, 15, 1046–1060, doi:10.3762/bjoc.15.102

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  • sequence of larger glycans [1][2][3]. Some galectins contain one CRD and occur as monomers or dimers, including galectins -1, -2, -7, -10 and -13 in humans. Others contain 2 different CRDs within the same peptide sequence and include galectins -4, -8, -9 and -12. Galectin-3 contains one CRD and a long N
  • ]. Galectin-1 has a marked preference for binding N-linked glycans, while galectin-3 binds both O-linked and N-linked glycans [5]. Galectins play many biological roles in the body and one important and well-understood function is the cross-linking of cell-surface glycoproteins through binding to O and N
  • -linked glycans on the cell surface. Surface proteins such as integrins [6][7], vascular endothelial growth factor receptor [8], and lysosome-associated membrane proteins [9] are known to be crosslinked by galectins, giving galectins a modulating role in cell adhesion, blood vessel growth and cellular
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Published 07 May 2019

Design and synthesis of multivalent α-1,2-trimannose-linked bioerodible microparticles for applications in immune response studies of Leishmania major infection

  • Chelsea L. Rintelmann,
  • Tara Grinnage-Pulley,
  • Kathleen Ross,
  • Daniel E. K. Kabotso,
  • Angela Toepp,
  • Anne Cowell,
  • Christine Petersen,
  • Balaji Narasimhan and
  • Nicola Pohl

Beilstein J. Org. Chem. 2019, 15, 623–632, doi:10.3762/bjoc.15.58

Graphical Abstract
  • system recognizes parasite surface glycoconjugates, or pathogen-associated molecular patterns (PAMPs), to build an immune response against the parasite and impede disease progression. Antigen presenting cells (APCs) recognize these PAMPs as pathogenic as compared to host glycans making these moieties
  • vary with Leishmania species (>20 species) and life stage of the pathogen, making it challenging to define how the capping sugars interact and modulate host immune responses [21][22][23][24]. Since these cell-surface glycans are structurally diverse and difficult to isolate in appreciable quantities
  • , synthetic pathogen-associated carbohydrate probes are necessary to understand the LPG structure-to-function relationship. These synthetic oligosaccharides also provide a structurally homogeneous standard to study how these glycans interact with the host immune system in an effort to develop effective anti
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Published 11 Mar 2019

Lectins of Mycobacterium tuberculosis – rarely studied proteins

  • Katharina Kolbe,
  • Sri Kumar Veleti,
  • Norbert Reiling and
  • Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2019, 15, 1–15, doi:10.3762/bjoc.15.1

Graphical Abstract
  • modifications of glycocalyx proteins are N-glycans (asparagine-linked) and O-glycans (serine- or threonine-linked), while glycosphingolipids are the major subclass of glycosylated lipids in the cell membrane of human cells (Figure 2). While many core elements of glycocalyx oligosaccharides are conserved between
  • host proteins and cell types, for example the invariant N-acetyl-D-glucosamine or N-acetyl-D-galactosamine residues that attach N- or O-glycans, respectively, to the peptide side chains, the large variety and possible permutations of “capping” residues (for example D-mannopyranosides, D
  • -containing glycans were detected as potential carbohydrate ligands for the ALS1 protein [88]. Intriguingly, Rv1753 is described as essential for in vitro growth of Mtb, as detected by transposon mutagenesis studies [89][90]. However, no further biochemical or genetic data are available for either Rv1753 or
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Published 02 Jan 2019

Synthesis of 1,4-imino-L-lyxitols modified at C-5 and their evaluation as inhibitors of GH38 α-mannosidases

  • Maroš Bella,
  • Sergej Šesták,
  • Ján Moncoľ,
  • Miroslav Koóš and
  • Monika Poláková

Beilstein J. Org. Chem. 2018, 14, 2156–2162, doi:10.3762/bjoc.14.189

Graphical Abstract
  • swainsonine, interferes with the glycosylation pathway where it specifically inhibits GH38 glycoside hydrolases [23][24]. Up to date, swainsonine is the most potent Golgi mannosidase II (GMII) inhibitor. It is known that inhibition of the biosynthesis of complex N-glycans in the Golgi apparatus influences
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Published 17 Aug 2018

Synthetic avenues towards a tetrasaccharide related to Streptococcus pneumonia of serotype 6A

  • Aritra Chaudhury,
  • Mana Mohan Mukherjee and
  • Rina Ghosh

Beilstein J. Org. Chem. 2018, 14, 1095–1102, doi:10.3762/bjoc.14.95

Graphical Abstract
  • ; oligosaccharides; stereoselectivity; total synthesis; Introduction Complex glycans serve as attractive targets for carbohydrate-based vaccines and therapeutics [1][2][3]. Streptococcus pneumonia (SPn) has been posing a serious threat in recent times. It is a major cause of pneumonia, bacteraemia, and meningitis
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Published 17 May 2018

Synthetic and semi-synthetic approaches to unprotected N-glycan oxazolines

  • Antony J. Fairbanks

Beilstein J. Org. Chem. 2018, 14, 416–429, doi:10.3762/bjoc.14.30

Graphical Abstract
  • for any further protecting group manipulations, and simplifying synthetic strategies. As an alternative to total synthesis, significant quantities of several structurally complicated N-glycans can be isolated from natural sources, such as egg yolks and soy bean flour. Enzymatic transformations of
  • these materials, in concert with DMC-mediated oxazoline formation as a final step, allow access to a selection of N-glycan oxazoline structures both in larger quantities and in a more expedient fashion than is achievable by total synthesis. Keywords: DMC, ENGase; glycosyl oxazolines; N-glycans
  • ] (ENGases, EC 3.2.1.96), a class of enzyme which specifically cleave between the innermost two GlcNAc residues of N-glycans attached to N-linked glycoproteins, all operate via a two-step mechanism involving neighbouring group participation of the 2-acetamide group and an oxazoline as a high energy
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Published 15 Feb 2018

What contributes to an effective mannose recognition domain?

  • Christoph P. Sager,
  • Deniz Eriş,
  • Martin Smieško,
  • Rachel Hevey and
  • Beat Ernst

Beilstein J. Org. Chem. 2017, 13, 2584–2595, doi:10.3762/bjoc.13.255

Graphical Abstract
  • human immune system (Table 1, A–F) recognize a broader spectrum of binding partners (i.e., various pathogenic oligosaccharides), bacterial CRDs G–I strive for tight binding to host glycans to improve their chances of survival. To achieve these enhanced affinities, pathogens apply a variety of strategies
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Published 04 Dec 2017

Preactivation-based chemoselective glycosylations: A powerful strategy for oligosaccharide assembly

  • Weizhun Yang,
  • Bo Yang,
  • Sherif Ramadan and
  • Xuefei Huang

Beilstein J. Org. Chem. 2017, 13, 2094–2114, doi:10.3762/bjoc.13.207

Graphical Abstract
  • addition, one-pot protocols have been developed that have enabled multiple-step glycosylations in the same reaction flask without the need for intermediate purification. Complex glycans containing both 1,2-cis and 1,2-trans linkages, branched oligosaccharides, uronic acids, sialic acids, modifications such
  • needed [3]. However, this is hampered by the limited availability of complex glycans from nature. Thus, chemical synthesis is a powerful approach to provide much needed samples to enable biological studies [4]. Traditional carbohydrate synthesis is commonly carried out from the reducing end to the non
  • glycolipid family including LewisX pentasaccharide 117, dimeric LewisX 118 [63], tristearoyl lipomannan 119 [64], gangliosides GM1 120 [65] and GM2 121 (Figure 5) [66], microbial glycans such as the heptasaccharide repeating unit of type V group B Streptococcus capsular polysaccharide 122 [67], β-glucan
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Published 09 Oct 2017

Intramolecular glycosylation

  • Xiao G. Jia and
  • Alexei V. Demchenko

Beilstein J. Org. Chem. 2017, 13, 2028–2048, doi:10.3762/bjoc.13.201

Graphical Abstract
  • proteins in the human body are glycosylated [3], and cells display a multitude of glycostructures [4]. Since glycan and glycoconjugate biomarkers are present in all body fluids, they offer a fantastic opportunity for diagnostics. Changes in the level of glycans, as well as changes in glycosylation and
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Published 29 Sep 2017

Enzymatic synthesis of glycosides: from natural O- and N-glycosides to rare C- and S-glycosides

  • Jihen Ati,
  • Pierre Lafite and
  • Richard Daniellou

Beilstein J. Org. Chem. 2017, 13, 1857–1865, doi:10.3762/bjoc.13.180

Graphical Abstract
  • already successfully applied to the biocatalysed synthesis of thiodi- or -trisaccharides [68][69][70][71][72], neo-thioglycoprotein [73], or even simple thioglycosides with potent inhibitory properties [74]. More complex biomolecules were also obtained like glycans or glycopolymers [75], or even rarer
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Published 05 Sep 2017

Strategies toward protecting group-free glycosylation through selective activation of the anomeric center

  • A. Michael Downey and
  • Michal Hocek

Beilstein J. Org. Chem. 2017, 13, 1239–1279, doi:10.3762/bjoc.13.123

Graphical Abstract
  • ligation of an oxazoline donor and commercially available RNase B protein (with the glycans curtailed to a single GlcNAc moiety [17]) as the acceptor [16]. The beauty of this work extends beyond the enzymatic glycosylation reaction. We point out that the oxazoline functionality was installed chemically in
  • conditions were feasible for the synthesis of glycosyl azides which are highly useful precursors for N-linked glycans [95] or Cu-catalyzed cycloadditions with alkynes (as shown above) [85]. By using tetrabutylammonium chloride and an amine base the highly reactive chlorinated intermediate forms that can be
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Published 27 Jun 2017

Glycoscience@Synchrotron: Synchrotron radiation applied to structural glycoscience

  • Serge Pérez and
  • Daniele de Sanctis

Beilstein J. Org. Chem. 2017, 13, 1145–1167, doi:10.3762/bjoc.13.114

Graphical Abstract
  • glycosylated, whereas proteins expressed in E. coli do not contain any glycan chains. For proteins that require post-translational modification, eukaryotic expression systems are usually preferred [30]. The crystallization of glycoproteins faces several obstacles, including the micro-heterogenity of glycans at
  • -Asp form was present. There are other cases where crystallization may be facilitated by the presence of glycans that form stabilizing intermolecular contacts within the crystal. Platforms for the expression and crystallization of glycoproteins are available and can typically be successful in a few
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Published 14 Jun 2017

Glyco-gold nanoparticles: synthesis and applications

  • Federica Compostella,
  • Olimpia Pitirollo,
  • Alessandro Silvestri and
  • Laura Polito

Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100

Graphical Abstract
  • space glycans from the Au surface is another fundamental factor to take into consideration in GAuNP design. Generally, the majority of the spacers are thiol-linkers, exploiting the strong soft–soft interaction between gold and sulfur. The spacer has the crucial role to stabilize GAuNPs in the
  • determination of the binding selectivity for human and avian influenza (H1N1 and H7N9), by using modified glycans (lactose, α(2,3)Neu5AcLacNAc and α(2,6)Neu5AcLacNAc) to introduce the active moieties on the gold monolayer. The SERS spectra registered with changes in the 1400–1600 and 1000–1200 cm−1 bands were
  • system in response to pathogens mediated by lectins, like DC-SIGN. Mammalian cell surface lectins, expressed on the surface of dendritic cells (DC) and macrophages, recognize in a multivalent way a vast array of glycans on the exterior of pathogens. Natural carbohydrate ligands include high-mannose N
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Published 24 May 2017

Expression, purification and structural analysis of functional GABA transporter 1 using the baculovirus expression system

  • Jing Hu,
  • Chris Weise,
  • Christoph Böttcher,
  • Hua Fan and
  • Jian Yin

Beilstein J. Org. Chem. 2017, 13, 874–882, doi:10.3762/bjoc.13.88

Graphical Abstract
  • GAT1 demonstrates that this single polypeptide contains twelve TM domains connected by hydrophilic loops with the amino and carboxy-termini residing in the cytoplasm [9][10]. Additionally, the GAT1 protein contains three conserved N-glycosylation sites [9]. The role of N-linked glycans in the GABA
  • Galanthusnivalis agglutinin (GNA, digoxigenin-conjugated lectin) (Figure 1F), indicating the predominance of the paucimannose structure in insect cells. In contrast, mammalian N-glycans have terminal sialic acid residues with more antennal diversity. The band at approximately 250 kDa corresponds to an oligomeric
  • but not the terminal trimming of N-glycans is involved in the regulation of the correct membrane glycoprotein folding since the inhibition of N-glycosylation processing by 1-deoxymannojirimycin (dMM) results in a mannose-rich type of N-glycan that does not affect either the protein stability or
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Published 11 May 2017

O-Alkylated heavy atom carbohydrate probes for protein X-ray crystallography: Studies towards the synthesis of methyl 2-O-methyl-L-selenofucopyranoside

  • Roman Sommer,
  • Dirk Hauck,
  • Annabelle Varrot,
  • Anne Imberty,
  • Markus Künzler and
  • Alexander Titz

Beilstein J. Org. Chem. 2016, 12, 2828–2833, doi:10.3762/bjoc.12.282

Graphical Abstract
  • glycans in pathogens or parasites, numerous other lectins recognize such O-alkylated ligands, e.g., the pilus adhesin from Pseudomonas aeruginosa PAK [31] or PapG from Escherichia coli [32]. In contrast, methylation of lectin ligands can also prevent binding, as observed with O-methylated fucose and
  • mannose for P. aeruginosa LecB or B. cenocepacia BC2L-A [33]. Thus, O-methylation of glycans can tune biological recognition events. In contrast to the literature reports on the synthesis of unmodified seleno glycosides, the synthesis of selectively O-alkylated derivatives to study their interactions with
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Published 22 Dec 2016

Automated glycan assembly of a S. pneumoniae serotype 3 CPS antigen

  • Markus W. Weishaupt,
  • Stefan Matthies,
  • Mattan Hurevich,
  • Claney L. Pereira,
  • Heung Sik Hahm and
  • Peter H. Seeberger

Beilstein J. Org. Chem. 2016, 12, 1440–1446, doi:10.3762/bjoc.12.139

Graphical Abstract
  • ]. Automated glycan assembly builds on monomeric building blocks that are incorporated during iterative glycosylations [28][29]. Here, a set of building blocks was identified that can be employed interchangeably in the automated syntheses of a wide variety of biologically relevant glycans. To minimize the post
  • - and trisaccharides while retaining all benzoyl esters. The introduction of an activator washing step prior to each glycosylation greatly increased the reproducibility of the automated syntheses and is envisioned to increase efficacy of AGA for many other biologically relevant glycans in the future. In
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Published 12 Jul 2016

Synthesis and in vitro cytotoxicity of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine

  • Štěpán Horník,
  • Lucie Červenková Šťastná,
  • Petra Cuřínová,
  • Jan Sýkora,
  • Kateřina Káňová,
  • Roman Hrstka,
  • Ivana Císařová,
  • Martin Dračínský and
  • Jindřich Karban

Beilstein J. Org. Chem. 2016, 12, 750–759, doi:10.3762/bjoc.12.75

Graphical Abstract
  • -2-azido-hexopyranoses have potential as synthons in oligosaccharide assembly. Keywords: amino sugars; cytotoxicity; fluorinated carbohydrates; fluorine; hexosamines; Introduction Derivatives of D-glucosamine (GlcN) and D-galactosamine (GalN) are essential amino sugar components of glycans in
  • glycoproteins, glycolipids and proteoglycans. As such, they participate in functions performed by cell-surface glycans including cell adhesion and signaling [1]. Unnatural analogs of these amino sugars prepared by a selective replacement of a hydroxy group by fluorine have proved valuable tools to perturb
  • 4-fluoro analogs of D-glucosamines 1–3, D-galactosamine 4, and 6-fluoro-D-galactosamine 9 (Figure 1) acted as metabolic inhibitors of the biosynthesis of cell-surface O- and N-linked glycans (including their lactosamine and sialyl LewisX terminal epitopes) [2][3][10][11], and glycosaminoglycans [3
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Published 20 Apr 2016

Elucidation of a masked repeating structure of the O-specific polysaccharide of the halotolerant soil bacteria Azospirillum halopraeferens Au4

  • Elena N. Sigida,
  • Yuliya P. Fedonenko,
  • Alexander S. Shashkov,
  • Nikolay P. Arbatsky,
  • Evelina L. Zdorovenko,
  • Svetlana A. Konnova,
  • Vladimir V. Ignatov and
  • Yuriy A. Knirel

Beilstein J. Org. Chem. 2016, 12, 636–642, doi:10.3762/bjoc.12.62

Graphical Abstract
  • and/or methylation of the rhizobial cell surface glycans depends on the growth phase [36] and cultivation conditions (in planta or ex planta) [26]. These modifications may promote attachment of the bacteria to the roots by an increase of the hydrophobicity of their cell surface. In turn, the increase
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Published 04 Apr 2016

Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives

  • Maroš Bella,
  • Miroslav Koóš and
  • Chun-Hung Lin

Beilstein J. Org. Chem. 2015, 11, 1547–1552, doi:10.3762/bjoc.11.170

Graphical Abstract
  • ][4]. In addition, the role played by the glycoconjugates changes markedly during disease development such as malignant transformation [5], cancer cell proliferation and metastases spreading [6]. Since glycosyltransferases (GTs) are entailed in the biosynthesis of glycans and glycoconjugates, which
  • unknown [7]. In general, GTs transfer sugar nucleotide donors onto suitable acceptors during the biosynthesis of glycans and glycoconjugates [8]. Both donor and acceptor substrates are recognized by GTs binding pockets. For instance, in the course of biosynthesis of complex and hybrid oligosaccharides
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Published 04 Sep 2015

DNA display of glycoconjugates to emulate oligomeric interactions of glycans

  • Alexandre Novoa and
  • Nicolas Winssinger

Beilstein J. Org. Chem. 2015, 11, 707–719, doi:10.3762/bjoc.11.81

Graphical Abstract
  • Alexandre Novoa Nicolas Winssinger Department of Organic Chemistry, NCCR Chemical Biology, University of Geneva 30, quai Ernest Ansermet, 1211 Geneva, Switzerland 10.3762/bjoc.11.81 Abstract Glycans (carbohydrate portion of glycoproteins and glycolipids) frequently exert their function through
  • surface glycans are important actors in cellular recognition and have been implicated in numerous events such as fertilization, embryonic development, lymphocyte trafficking and cancer metastasis [1][2][3][4]. In contrast to many small molecule ligands where a functional output is often the product of a
  • single high-affinity interaction with a target macromolecule, glycans’ interactions with glycan-binding proteins (GPB) or lectins are typically low affinity. However high avidity and specificity is achieved through the concerted interactions of multiple ligands with well-defined spatial geometry [5]. The
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Published 11 May 2015

Automated solid-phase synthesis of oligosaccharides containing sialic acids

  • Chian-Hui Lai,
  • Heung Sik Hahm,
  • Chien-Fu Liang and
  • Peter H. Seeberger

Beilstein J. Org. Chem. 2015, 11, 617–621, doi:10.3762/bjoc.11.69

Graphical Abstract
  • -phase synthesis; Introduction N-Acetylneuraminic acid (sialic acid, Neu5Ac) is an important component of mammalian glycans and key to many recognition events of biomedical relevance including cell–cell recognition, signaling, and the immune response [1]. Sialic acids are present in tumor-associated
  • glycopeptides [6], glycosaminoglycans [7][8][9], and chains as long as 30-mers [10]. Key to automated assembly is the identification of reliable monosaccharide building blocks to construct particular linkages. To date, α-(2,3)- and α-(2,6)-sialylated glycans have been accessible by automation only via
  • 13 in 40% overall yield for four steps based on resin loading. The absolute anomeric configurations of glycans that contain sialylic acid were determined by recording the long-range coupling constants of C1 with axial H3 (3J C-1,H-3ax) using 1D coupled HMQC experiments. Coupling constant higher than
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Published 04 May 2015
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