Multivalent glycosystems for nanoscience

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Editor: Prof. Thisbe K. Lindhorst
Christian-Albrechts-Universität zu Kiel
 
Carbohydrates constitute the most abundant class of biomolecules on Earth. They exist as small mono- or oligo-saccharides, as large and highly complex polysaccharides, and in conjugation with, for example, proteins and lipids, forming a kingdom of glycoconjugates that are found on every cell surface. It is now generally considered important to be able to synthesize carbohydrates and glycoconjugates, to analyze their structures, and to advance our understanding of the biology of carbohydrates in living systems. The Thematic Series “Synthesis in the glycosciences” and “Synthesis in the glycosciences II” have impressively documented the state of the art in this field of research. Now, a third Thematic Series is presented in which the structural world of natural sugars has been extended towards artificial carbohydrate architectures to achieve potential innovations offered by glycoconjugates. For instance, multivalent glycoconjugates can be used as anti-adhesive drugs against microbial infections. They could be developed into bioimaging agents that can target specific tissues. Indeed, they will certainly find applications in materials science and in medicine, for example, in drug delivery or diagnostics.

See also the Thematic Series:
Multivalency as a chemical organization and action principle

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Multivalent glycosystems for nanoscience

  • Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2014, 10, 2345–2347, doi:10.3762/bjoc.10.244

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Published 08 Oct 2014

Synthesis of a sucrose dimer with enone tether; a study on its functionalization

  • Zbigniew Pakulski,
  • Norbert Gajda,
  • Magdalena Jawiczuk,
  • Jadwiga Frelek,
  • Piotr Cmoch and
  • Sławomir Jarosz

Beilstein J. Org. Chem. 2014, 10, 1246–1254, doi:10.3762/bjoc.10.124

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Published 28 May 2014

Human dendritic cell activation induced by a permannosylated dendron containing an antigenic GM3-lactone mimetic

  • Renato Ribeiro-Viana,
  • Elena Bonechi,
  • Javier Rojo,
  • Clara Ballerini,
  • Giuseppina Comito,
  • Barbara Richichi and
  • Cristina Nativi

Beilstein J. Org. Chem. 2014, 10, 1317–1324, doi:10.3762/bjoc.10.133

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Published 10 Jun 2014

Design and synthesis of multivalent neoglycoconjugates by click conjugations

  • Feiqing Ding,
  • Li Ji,
  • Ronny William,
  • Hua Chai and
  • Xue-Wei Liu

Beilstein J. Org. Chem. 2014, 10, 1325–1332, doi:10.3762/bjoc.10.134

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Published 10 Jun 2014

Glycosystems in nanotechnology: Gold glyconanoparticles as carrier for anti-HIV prodrugs

  • Fabrizio Chiodo,
  • Marco Marradi,
  • Javier Calvo,
  • Eloisa Yuste and
  • Soledad Penadés

Beilstein J. Org. Chem. 2014, 10, 1339–1346, doi:10.3762/bjoc.10.136

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Published 12 Jun 2014

Molecular recognition of surface-immobilized carbohydrates by a synthetic lectin

  • Melanie Rauschenberg,
  • Eva-Corrina Fritz,
  • Christian Schulz,
  • Tobias Kaufmann and
  • Bart Jan Ravoo

Beilstein J. Org. Chem. 2014, 10, 1354–1364, doi:10.3762/bjoc.10.138

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Published 16 Jun 2014

Biantennary oligoglycines and glyco-oligoglycines self-associating in aqueous medium

  • Svetlana V. Tsygankova,
  • Alexander A. Chinarev,
  • Alexander B. Tuzikov,
  • Nikolai Severin,
  • Alexey A. Kalachev,
  • Juergen P. Rabe,
  • Alexandra S. Gambaryan and
  • Nicolai V. Bovin

Beilstein J. Org. Chem. 2014, 10, 1372–1382, doi:10.3762/bjoc.10.140

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Published 17 Jun 2014

Synthesis of the first examples of iminosugar clusters based on cyclopeptoid cores

  • Mathieu L. Lepage,
  • Alessandra Meli,
  • Anne Bodlenner,
  • Céline Tarnus,
  • Francesco De Riccardis,
  • Irene Izzo and
  • Philippe Compain

Beilstein J. Org. Chem. 2014, 10, 1406–1412, doi:10.3762/bjoc.10.144

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Published 23 Jun 2014

Carbohydrate PEGylation, an approach to improve pharmacological potency

  • M. Eugenia Giorgi,
  • Rosalía Agusti and
  • Rosa M. de Lederkremer

Beilstein J. Org. Chem. 2014, 10, 1433–1444, doi:10.3762/bjoc.10.147

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Published 25 Jun 2014

Multichromophoric sugar for fluorescence photoswitching

  • Stéphane Maisonneuve,
  • Rémi Métivier,
  • Pei Yu,
  • Keitaro Nakatani and
  • Juan Xie

Beilstein J. Org. Chem. 2014, 10, 1471–1481, doi:10.3762/bjoc.10.151

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Published 30 Jun 2014

Postsynthetic functionalization of glycodendrons at the focal point

  • Thisbe K. Lindhorst and
  • Katharina Elsner

Beilstein J. Org. Chem. 2014, 10, 1482–1487, doi:10.3762/bjoc.10.152

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Published 01 Jul 2014

Efficient routes toward the synthesis of the D-rhamno-trisaccharide related to the A-band polysaccharide of Pseudomonas aeruginosa

  • Aritra Chaudhury,
  • Sajal K. Maity and
  • Rina Ghosh

Beilstein J. Org. Chem. 2014, 10, 1488–1494, doi:10.3762/bjoc.10.153

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Published 01 Jul 2014

Bis(β-lactosyl)-[60]fullerene as novel class of glycolipids useful for the detection and the decontamination of biological toxins of the Ricinus communis family

  • Hirofumi Dohi,
  • Takeru Kanazawa,
  • Akihiro Saito,
  • Keita Sato,
  • Hirotaka Uzawa,
  • Yasuo Seto and
  • Yoshihiro Nishida

Beilstein J. Org. Chem. 2014, 10, 1504–1512, doi:10.3762/bjoc.10.155

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Published 03 Jul 2014

Why a diaminopyrrolic tripodal receptor binds mannosides in acetonitrile but not in water?

  • Diogo Vila-Viçosa,
  • Oscar Francesconi and
  • Miguel Machuqueiro

Beilstein J. Org. Chem. 2014, 10, 1513–1523, doi:10.3762/bjoc.10.156

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Published 03 Jul 2014

Synthesis and solvodynamic diameter measurements of closely related mannodendrimers for the study of multivalent carbohydrate–protein interactions

  • Yoann M. Chabre,
  • Alex Papadopoulos,
  • Alexandre A. Arnold and
  • René Roy

Beilstein J. Org. Chem. 2014, 10, 1524–1535, doi:10.3762/bjoc.10.157

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Published 04 Jul 2014

A promising cellulose-based polyzwitterion with pH-sensitive charges

  • Thomas Elschner and
  • Thomas Heinze

Beilstein J. Org. Chem. 2014, 10, 1549–1556, doi:10.3762/bjoc.10.159

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Published 08 Jul 2014

Orthogonal dual thiol–chloroacetyl and thiol–ene couplings for the sequential one-pot assembly of heteroglycoclusters

  • Michele Fiore,
  • Gour Chand Daskhan,
  • Baptiste Thomas and
  • Olivier Renaudet

Beilstein J. Org. Chem. 2014, 10, 1557–1563, doi:10.3762/bjoc.10.160

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Published 08 Jul 2014

Multivalent scaffolds induce galectin-3 aggregation into nanoparticles

  • Candace K. Goodman,
  • Mark L. Wolfenden,
  • Pratima Nangia-Makker,
  • Anna K. Michel,
  • Avraham Raz and
  • Mary J. Cloninger

Beilstein J. Org. Chem. 2014, 10, 1570–1577, doi:10.3762/bjoc.10.162

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Published 10 Jul 2014

Photoswitchable precision glycooligomers and their lectin binding

  • Daniela Ponader,
  • Sinaida Igde,
  • Marko Wehle,
  • Katharina Märker,
  • Mark Santer,
  • David Bléger and
  • Laura Hartmann

Beilstein J. Org. Chem. 2014, 10, 1603–1612, doi:10.3762/bjoc.10.166

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Published 15 Jul 2014

Clicked and long spaced galactosyl- and lactosylcalix[4]arenes: new multivalent galectin-3 ligands

  • Silvia Bernardi,
  • Paola Fezzardi,
  • Gabriele Rispoli,
  • Stefania E. Sestito,
  • Francesco Peri,
  • Francesco Sansone and
  • Alessandro Casnati

Beilstein J. Org. Chem. 2014, 10, 1672–1680, doi:10.3762/bjoc.10.175

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Published 23 Jul 2014

Bifunctional dendrons for multiple carbohydrate presentation via carbonyl chemistry

  • Davide Bini,
  • Francesco Nicotra and
  • Laura Cipolla

Beilstein J. Org. Chem. 2014, 10, 1686–1691, doi:10.3762/bjoc.10.177

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Published 25 Jul 2014

Convergent synthetic methodology for the construction of self-adjuvanting lipopeptide vaccines using a novel carbohydrate scaffold

  • Vincent Fagan,
  • Istvan Toth and
  • Pavla Simerska

Beilstein J. Org. Chem. 2014, 10, 1741–1748, doi:10.3762/bjoc.10.181

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Published 30 Jul 2014

Synthesis of rigid p-terphenyl-linked carbohydrate mimetics

  • Maja Kandziora and
  • Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2014, 10, 1749–1758, doi:10.3762/bjoc.10.182

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Published 30 Jul 2014

Expeditive synthesis of trithiotriazine-cored glycoclusters and inhibition of Pseudomonas aeruginosa biofilm formation

  • Meriem Smadhi,
  • Sophie de Bentzmann,
  • Anne Imberty,
  • Marc Gingras,
  • Raoudha Abderrahim and
  • Peter G. Goekjian

Beilstein J. Org. Chem. 2014, 10, 1981–1990, doi:10.3762/bjoc.10.206

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Published 25 Aug 2014

Indium-mediated allylation in carbohydrate synthesis: A short and efficient approach towards higher 2-acetamido-2-deoxy sugars

  • Christopher Albler,
  • Ralph Hollaus,
  • Hanspeter Kählig and
  • Walther Schmid

Beilstein J. Org. Chem. 2014, 10, 2230–2234, doi:10.3762/bjoc.10.231

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Published 19 Sep 2014

Expanding the scope of cyclopropene reporters for the detection of metabolically engineered glycoproteins by Diels–Alder reactions

  • Anne-Katrin Späte,
  • Verena F. Schart,
  • Julia Häfner,
  • Andrea Niederwieser,
  • Thomas U. Mayer and
  • Valentin Wittmann

Beilstein J. Org. Chem. 2014, 10, 2235–2242, doi:10.3762/bjoc.10.232

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Published 22 Sep 2014

Synthesis and immunological evaluation of protein conjugates of Neisseria meningitidis X capsular polysaccharide fragments

  • Laura Morelli,
  • Damiano Cancogni,
  • Marta Tontini,
  • Alberto Nilo,
  • Sara Filippini,
  • Paolo Costantino,
  • Maria Rosaria Romano,
  • Francesco Berti,
  • Roberto Adamo and
  • Luigi Lay

Beilstein J. Org. Chem. 2014, 10, 2367–2376, doi:10.3762/bjoc.10.247

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Published 13 Oct 2014
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