Multivalent glycosystems for nanoscience

Thisbe K. Lindhorst

Editorial
Published 08 Oct 2014

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

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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

Full Research Paper
Published 28 May 2014

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1. Graphical Abstract
2. Figure 1: Examples of sucrose-based macrocycles.
  
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3. Figure 2: Synthesis of higher sugar precursors by a Wittig-type methodology.
  
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4. Scheme 1: Synthesis of higher sugar enone 10.
  
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5. Scheme 2: Synthesis of the diol 13 containing two sucrose units.
  
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6. Figure 3: CD spectra of in situ formed chiral complexes of 13 (green line), 14 (purple line) and 16 (blue lin...
  
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7. Scheme 3: Synthesis of model sucrose diols.
  
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Beilstein J. Org. Chem. 2014, 10, 1246–1254, doi:10.3762/bjoc.10.124

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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

Full Research Paper
Published 10 Jun 2014

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1. Graphical Abstract
2. Figure 1: Structure of GM₃-ganglioside 1, GM₃-lactone 2, GM₃-lactone mimetic 3, and GM₃-lactone mimetic conju...
  
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3. Scheme 1: Synthesis of the bifunctional multivalent glycodendron 5.
  
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4. Figure 2: Upper panels: percentage of expression of dendritic cell markers (HLA-DR ECD, CD80 FITC, CD86 PE an...
  
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Beilstein J. Org. Chem. 2014, 10, 1317–1324, doi:10.3762/bjoc.10.133

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Design and synthesis of multivalent neoglycoconjugates by click conjugations

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

Full Research Paper
Published 10 Jun 2014

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1. Graphical Abstract
2. Figure 1: Our reported strategy for quick access to 3-amino-2,3-dideoxysugars via regio- and stereoselective ...
  
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3. Figure 2: Synthetic modification of α-GalNAc linked glycopeptides to 3-tosylamino-2,3-dideoxyneoglycoconjugat...
  
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4. Figure 3: Our proposal for access to 3-tosylamino-2,3-dideoxyneoglycoconjugates via tandem hydroamination/gly...
  
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5. Scheme 1: Synthesis of propargyl 3-tosylamino-2,3-dideoxy-α-D-allohexopyranoside (2a).
  
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6. Scheme 2: Synthesis of divalent 3-tosylamino-2,3-dideoxyneoglycoconjugates 6a and 6b.
  
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7. Scheme 3: Synthesis of trivalent 3-tosylamino-2,3-dideoxyneoglycoconjugate 6c.
  
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Beilstein J. Org. Chem. 2014, 10, 1325–1332, doi:10.3762/bjoc.10.134

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

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

Full Research Paper
Published 12 Jun 2014

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1. Graphical Abstract
2. Figure 1: The prepared lamivudine (3TC) and abacavir (ABC) potential prodrugs and the corresponding 3TC- and ...
  
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3. Figure 2: Time course release of free 3TC and ABC from the corresponding GNPs in 1 N HCl, detected by HPLC–MS...
  
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4. Figure 3: Cellular experiments: The two graphs show the percentage of luciferase activity decrease in the pre...
  
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Beilstein J. Org. Chem. 2014, 10, 1339–1346, doi:10.3762/bjoc.10.136

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Molecular recognition of surface-immobilized carbohydrates by a synthetic lectin

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

Full Research Paper
Published 16 Jun 2014

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1. Graphical Abstract
2. Figure 1: Molecular structures of carbohydrates (NANA, Glc, Gal, Man) immobilized on epoxide SAMs, NANA-bindi...
  
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3. Figure 2: Schematic representation of the preparation of a simple carbohydrate microarray by μCP of amine-fun...
  
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4. Figure 3: Optical microscopy images of water droplets selectively condensed in the areas where (A) the NANA i...
  
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5. Figure 4: (A) AFM height image (zoom) of NANA ink in 10 μm stripes on an epoxide-terminated SAM; (B) Height p...
  
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6. Figure 5: Fluorescence images of bifunctional carbohydrate microarrays incubated with FITC-HisHis. (A) NANA (...
  
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7. Figure 6: Overlay of fluorescence images of bifunctional carbohydrate microarrays; (A) NANA (dots 10 × 5 μm) ...
  
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8. Figure 7: Fluorescence images of a microarray consisting of NANA (dots 5 × 3 μm) and Man (background). (A) In...
  
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9. Figure 8: Fluorescence images of a microarray of NANA (dots 5 × 3 μm) and Glc (background), first incubated w...
  
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Beilstein J. Org. Chem. 2014, 10, 1354–1364, doi:10.3762/bjoc.10.138

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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

Full Research Paper
Published 17 Jun 2014

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1. Graphical Abstract
2. Figure 1: The structure of biantennary oligoglycines and their glyco derivatives (sp = spacer group).
  
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3. Scheme 1: Synthesis of biantennary oligoglycines and their glycoderivatives.
  
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4. Figure 2: Dynamics of associate formation by biantennary oligoglycines Н-Gly_n-NH(СН₂)₁₀NH-Gly_n-Н. a) n = 4–5,...
  
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5. Figure 3: Raman spectra of a) [H-Gly₇-NHCH₂]₄C; b) H-Gly₄-NH(CH₂)₂NH-Gly₄-H; c) H-Gly₄-NH(CH₂)₁₀NH-Gly₄-H. Th...
  
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6. Figure 4: Model of the formation of tectomer layers by biantennary oligoglycines on a mica surface. The heigh...
  
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7. Figure 5: Growth of the tectomer formed by the peptide Н-Gly₄-NH(СН₂)₁₀-NHGly₄-Н (concentration 0.1 mg/mL) on...
  
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8. Figure 6: Growth of the tectomer formed by peptide Н-Gly₄-NH(СН₂)₁₀NH-Gly₄-Н (concentration 0.1 mg/mL) on a m...
  
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9. Figure 7: SFM images of associates formed by peptides а) Н-Gly₅-NH(СН₂)₂NH-Gly₅-Н and b) Н-Gly₅-NH(СН₂)₁₀NH-G...
  
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Beilstein J. Org. Chem. 2014, 10, 1372–1382, doi:10.3762/bjoc.10.140

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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

Letter
Published 23 Jun 2014

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1. Graphical Abstract
2. Figure 1: N-Bu-DNJ (1), azide-armed DNJ derivatives 5 and cyclopeptoid scaffolds 2–4.
  
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3. Scheme 1: Sub-monomer approach for the synthesis of cyclopeptoids 2–4: DIPEA = N,N-diisopropylethylamine; DIC...
  
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4. Scheme 2: Synthesis of DNJ clusters 10: (a) CuSO₄·5H₂O cat., sodium ascorbate, DMF/H₂O (5:1), MW, 80 °C; (b) ...
  
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5. Figure 2: i) Partial ¹H NMR spectrum (400 MHz, CD₃CN/CDCl₃ 9:1) of compound 9a; ii) Partial ¹H NMR spectrum (...
  
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6. Figure 3: Monovalent models 11 and 7-valent DNJ derivatives 12.
  
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Beilstein J. Org. Chem. 2014, 10, 1406–1412, doi:10.3762/bjoc.10.144

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Carbohydrate PEGylation, an approach to improve pharmacological potency

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

Review
Published 25 Jun 2014

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1. Graphical Abstract
2. Figure 1: Types of PEG utilized for derivatization of drugs and peptides.
  
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3. Figure 2: Activated PEG derivatives for conjugation.
  
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4. Scheme 1: Chemoenzymatic method for the preparation of PEG-CMP-SA, adapted from [32,33].
  
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5. Scheme 2: GlycoPEGylation by sequential in vitro, enzyme mediated, O-glycosylation followed by transfer of PE...
  
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6. Scheme 3: Chemical glycation of a protein and PEGylation after periodate oxidation, adapted from [34].
  
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7. Scheme 4: PEGylation of native glycosylated proteins after modification of the glycan. (A) Enzymatic modifica...
  
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8. Scheme 5: PEGylation of a pentofuranose derivative, adapted from [41].
  
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9. Scheme 6: Galactosyl PEGylation of polystyrene nanoparticles, adapted from [42].
  
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10. Figure 3: Mannosyl PEGylated polyethylenimine for delivery systems. (A) Mannose and PEG are independently lin...
  
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11. Figure 4: PEGylated mannose derivatives, adapted from [45].
  
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12. Scheme 7: PEGylation of lactose analogs [53].
  
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13. Scheme 8: Conjugation of lactose analogs with dendritic PEGs [54].
  
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14. Figure 5: PEGylated chitosan derivative, adapted from [61].
  
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15. Figure 6: Chitosan/PEG functionalized with a mannose at the distal end, adapted from [62].
  
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Beilstein J. Org. Chem. 2014, 10, 1433–1444, doi:10.3762/bjoc.10.147

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Multichromophoric sugar for fluorescence photoswitching

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

Full Research Paper
Published 30 Jun 2014

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1. Graphical Abstract
2. Figure 1: Requirements on absorption and emission spectral features of the photochromic and fluorescent units...
  
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3. Figure 2: Bifunctional fluorescent-photochromic molecules 1 and 2.
  
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4. Scheme 1: Synthesis of multichromophoric glucopyranoside 2.
  
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5. Figure 3: Absorption and fluorescence spectra of compounds 6, 9, and 2 in CH₃CN: (a) absorption spectrum of 6...
  
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6. Figure 4: Absorption and fluorescence changes of compound 2 (1.0 μM in CH₃CN) upon UV–visible irradiation: (a...
  
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7. Figure 5: Partial ¹H NMR spectra of compound 2 (11 μM in CD₃CN/DMSO-d₆ 4:1) before and after increasing irrad...
  
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8. Figure 6: (a) Fluorescence decays (λ_exc = 475 nm, λ_em = 610 nm) of compound 2-OF, and 2 after irradiation at ...
  
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Beilstein J. Org. Chem. 2014, 10, 1471–1481, doi:10.3762/bjoc.10.151

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Postsynthetic functionalization of glycodendrons at the focal point

Thisbe K. Lindhorst and
Katharina Elsner

Full Research Paper
Published 01 Jul 2014

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1. Graphical Abstract
2. Figure 1: a) Dendrons (right) are branched fragments of dendrimers (left), featuring a functional group (FG) ...
  
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3. Scheme 1: Synthesis of the starting material for postsynthetic focal point functionalization; published yield...
  
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4. Scheme 2: Initial syntheses of amphiphilic glycodendrons.
  
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5. Scheme 3: Postsynthetic focal modification of glycodendrons (I) using using olefin cross metathesis.
  
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6. Scheme 4: Postsynthetic focal modification of glycodendrons (II) using olefin cross metathesis.
  
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Beilstein J. Org. Chem. 2014, 10, 1482–1487, doi:10.3762/bjoc.10.152

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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

Full Research Paper
Published 01 Jul 2014

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1. Graphical Abstract
2. Figure 1: Repeating unit of the A-band polysaccharide of P. aeruginosa.
  
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3. Scheme 1: Preparation of the monomeric building blocks; reagents and conditions: i) Pyr., BzCl, 0 °C–rt; ii) ...
  
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4. Figure 2: Retrosynthetic analysis.
  
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5. Scheme 2: Sequential stepwise synthesis of the trisaccharide; reagents and conditions: i) TMSOTf, DCM, molecu...
  
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6. Scheme 3: Synthesis of the trisaccharide by sequential one-pot glycosylation reactions; reagents and conditio...
  
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7. Scheme 4: Synthesis of the target trisaccharide via global deoxygenation strategy; reagents and conditions: i...
  
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Beilstein J. Org. Chem. 2014, 10, 1488–1494, doi:10.3762/bjoc.10.153

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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

Full Research Paper
Published 03 Jul 2014

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1. Graphical Abstract
2. Figure 1: Structure of bis(β-lactosyl)-[60]fullerene (bis-Lac-C₆₀).
  
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3. Scheme 1: Synthesis of bis-Lac-C₆₀. Reagents and conditions: (a) 6-chloro-1-hexanol, TMSOTf, CH₂Cl₂, −40 °C, ...
  
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4. Figure 2: Precipitation assay of bis-Lac-C₆₀ colloidal solution. The tubes were allowed to stand for 10 min a...
  
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5. Figure 3: Schematic image for the quantitative analysis of ricin protein in the colloidal suspension of bis-L...
  
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6. Figure 4: A modified procedure for the rapid detection and the efficient decontamination of ricin and ricin-l...
  
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Beilstein J. Org. Chem. 2014, 10, 1504–1512, doi:10.3762/bjoc.10.155

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

Diogo Vila-Viçosa,
Oscar Francesconi and
Miguel Machuqueiro

Full Research Paper
Published 03 Jul 2014

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1. Graphical Abstract
2. Figure 1: Octyl α-D-mannoside (mannoside) and diaminopyrrolic tripodal receptor molecules. 2D and 3D represen...
  
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3. Figure 2: Full titration curve of the receptor (a) and the correspondent percentage of protonation in each ge...
  
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4. Figure 3: Diagram representing the population of all microstates at each number of titrable protons (n) prese...
  
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5. Figure 4: Radius of gyration (R_g) histograms for the receptor in water at pH 1.0, 3.0, 6.0, 10.0 and in ACN. ...
  
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6. Figure 5: Free energy profiles for the receptor at pH 1.0 (a), 6.0 (b), 10.0 (c) and ACN (d) using RMSD and R_g...
  
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7. Figure 6: Schematic representation of the receptor arms positions. Pyrrolic nitrogen atoms positions relative...
  
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8. Figure 7: Histogram of the hydrogen bonds between receptor and mannoside in ACN and water (at different proto...
  
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9. Figure 8: Distance histograms between the center of mass of the last 4 atoms of the carbon chain of the manno...
  
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10. Figure 9: Typical conformations in water and ACN. The selected conformations have 6 hydrogen bonds in ACN and...
  
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Beilstein J. Org. Chem. 2014, 10, 1513–1523, doi:10.3762/bjoc.10.156

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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

Full Research Paper
Published 04 Jul 2014

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1. Graphical Abstract
2. Scheme 1: Synthesis of mannosylated trimers 5 and 9 using trimesic acid core transformed into propargylated (2...
  
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3. Scheme 2: Divergent CuAAc “click reaction” between propargylated core 10 and azide 3 to afford 9-mer 12.
  
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4. Scheme 3: Divergent CuAAc synthesis of “extended” 9-mer 17 using phloroglucinol (13) as core, bromoacylated T...
  
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5. Scheme 4: Convergent synthesis of further “extended” 9-mer 21 using mannosylated bromoacyl dendron 18 transfo...
  
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6. Scheme 5: Convergent assembly of 27-mer 23 using key propargylated scaffold precursors 10 and mannosylated az...
  
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7. Figure 1: a) Decay of ¹H signal for the nonavalent mannosylated compound 12 in D₂O during the PFGSTE experime...
  
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Beilstein J. Org. Chem. 2014, 10, 1524–1535, doi:10.3762/bjoc.10.157

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A promising cellulose-based polyzwitterion with pH-sensitive charges

Thomas Elschner and
Thomas Heinze

Full Research Paper
Published 08 Jul 2014

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1. Graphical Abstract
2. Figure 1: Reaction scheme of the synthesis of anionic, cationic, and ampholytic cellulose carbamates (substit...
  
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3. Figure 2: ¹³C NMR spectra of (3-ethoxy-3-oxopropyl)(N-Boc-2-aminoethyl)- (4), (2-carboxyethyl)(N-Boc-2-aminoe...
  
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4. Figure 3: Acid–base titration of (3-ethoxy-3-oxopropyl)(2-aminoethyl)cellulose carbamate (6, 0.4%) in 0.2 M a...
  
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5. Figure 4: Acid–base titration of (2-carboxyethyl)(2-aminoethyl)cellulose carbamate (7a, 0.4%) in 0.2 M aqueou...
  
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6. Figure 5: Acid–base titration of (2-carboxyethyl)(N-Boc-2-aminoethyl)-cellulose carbamate (5, 0.1%) from pH 6...
  
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7. Figure 6: Acid–base titration of (2-carboxyethyl)(2-aminoethyl)cellulose carbamate (7a, 0.4% in water) from p...
  
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8. Figure 7: Titration of (2-carboxyethyl)(2-aminoethyl)cellulose carbamate (7a, 0.1% in water) at pH 11.5 with ...
  
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9. Figure 8: Titration of (2-carboxyethyl)(2-aminoethyl)cellulose carbamate (7a, 0.1% in water) and polyDADMAC (...
  
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Beilstein J. Org. Chem. 2014, 10, 1549–1556, doi:10.3762/bjoc.10.159

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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

Full Research Paper
Published 08 Jul 2014

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1. Graphical Abstract
2. Figure 1: Chemical strategy for the construction of heteroglycoclusters.
  
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3. Scheme 1: Stepwise (Route A) and sequential one-pot (Route B) synthesis of hGCs.
  
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4. Scheme 2: Synthesis of hGCs 11 and 13.
  
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5. Figure 2: RP-HPLC profile of the one-pot synthesis of hGC 11 (linear A–B gradient: 5 to 100% B in 20 min, λ =...
  
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Beilstein J. Org. Chem. 2014, 10, 1557–1563, doi:10.3762/bjoc.10.160

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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

Full Research Paper
Published 10 Jul 2014

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1. Graphical Abstract
2. Scheme 1: Synthesis of isothiocyanato-functionalized lactoside 1.
  
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3. Scheme 2: Synthesis of carbohydrate-functionalized PAMAM dendrimers. (Values for m and for x equivalents adde...
  
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4. Figure 1: Effective diameter of galectin-3/glycodendrimer aggregates (DLS). Final concentration of galectin-3...
  
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5. Figure 2: Schematic representation of galectin-3/glycodendrimer aggregates at varying stoichiometries.
  
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6. Figure 3: Fluorescence microscopy images of labelled particles. Microbead standards at similar exposure times...
  
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7. Figure 4: Aggregate diameter distribution of fluorescence microscopy images; 31 μM galectin-3 and 0.14 μM (a) ...
  
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Beilstein J. Org. Chem. 2014, 10, 1570–1577, doi:10.3762/bjoc.10.162

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Photoswitchable precision glycooligomers and their lectin binding

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

Full Research Paper
Published 15 Jul 2014

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1. Graphical Abstract
2. Figure 1: Synthesis of photoswitchable precision glycooligomers via stepwise addition of building blocks on s...
  
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3. Figure 2: Characterization of the E → Z photoisomerization (λ = 360 nm) of Azo-Gal(1,3,5)-5 in buffer solutio...
  
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4. Figure 3: Structural models of Azo-Gal(1,3)-3 and Azo-Gal(1,3,5)-5 in (a) E- and (b) all-Z-configurations of ...
  
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Beilstein J. Org. Chem. 2014, 10, 1603–1612, doi:10.3762/bjoc.10.166

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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

Full Research Paper
Published 23 Jul 2014

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1. Graphical Abstract
2. Figure 1: Lactosylthioureidocalix[4]arenes I–III used to inhibit Gal-3 [20,21].
  
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3. Figure 2: The new glycocalix[4]arenes 1–4 synthesized in this study.
  
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4. Scheme 1: Synthesis of the cone galactosylcalix[4]arenes 1. Reaction conditions: (i) DCC, DMAP, CH₂Cl₂, under...
  
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5. Scheme 2: Synthesis of the cone galactosylcalix[4]arenes 2. Reaction conditions: (i) DIPEA, CH₂Cl₂, rt, 6 h, ...
  
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6. Scheme 3: Synthesis of the cone lactosylcalix[4]arenes 3. Reaction conditions: (i) NaN₃, n-Bu₄NI, DMF, 90 °C,...
  
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7. Scheme 4: Synthesis of the 1,3-alternate lactosylcalix[4]arenes 4. Reaction conditions: (i) EDC, CH₂Cl₂/py (7...
  
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8. Figure 3: SPR sensorgrams of binding experiment between immobilized Gal-3 and glycocalixarenes 1, 3 and 4.
  
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9. Figure 4: a) Relative affinities of glycocalixarene 1, 3, 4 (1 mM) towards Gal-3, expressed in terms of the i...
  
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Beilstein J. Org. Chem. 2014, 10, 1672–1680, doi:10.3762/bjoc.10.175

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Bifunctional dendrons for multiple carbohydrate presentation via carbonyl chemistry

Davide Bini,
Francesco Nicotra and
Laura Cipolla

Letter
Published 25 Jul 2014

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1. Graphical Abstract
2. Figure 1: Synthesized G0, G1 and G2 dendrons and functionalized saccharides used for carbonyl conjugation.
  
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3. Scheme 1: Schematic depiction of dendron conjugation to saccharides by carbonyl chemistry.
  
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4. Scheme 2: Synthesis of the dendrons.
  
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5. Scheme 3: Dendron conjugation to fucose moieties by reductive amination. Reagents and conditions: a) 4, 3 M Na...
  
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6. Scheme 4: Dendron conjugation to fucose via oxime ligation (buffer = citrate buffer).
  
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Beilstein J. Org. Chem. 2014, 10, 1686–1691, doi:10.3762/bjoc.10.177

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

Vincent Fagan,
Istvan Toth and
Pavla Simerska

Full Research Paper
Published 30 Jul 2014

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1. Graphical Abstract
2. Scheme 1: Convergent construction of self-adjuvanting vaccines bearing multiple copies of a B cell epitope.
  
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3. Scheme 2: Synthesis of carbohydrate building block 1.
  
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4. Scheme 3: (A) Lipidation of Fmoc-Lys-OH with lauroyl chloride: (B) Lipidation of Fmoc-Lys-OH with sulfonic-ca...
  
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5. Scheme 4: Convergent synthesis of self-adjuvanting vaccine candidate 10 consisting of lipidic adjuvanting moi...
  
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6. Figure 1: Analytical HPLCs of copper-catalyzed alkyne–azide cycloaddition reaction at the start (top) and aft...
  
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7. Scheme 5: Convergent synthesis of self-adjuvanting vaccine candidate 12 consisting of lipidic adjuvanting moi...
  
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Beilstein J. Org. Chem. 2014, 10, 1741–1748, doi:10.3762/bjoc.10.181

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Synthesis of rigid p-terphenyl-linked carbohydrate mimetics

Maja Kandziora and
Hans-Ulrich Reissig

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Published 30 Jul 2014

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1. Graphical Abstract
2. Scheme 1: Approach to divalent carbohydrate mimetics 1 with rigid spacer and monovalent analogues 2.
  
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3. Scheme 2: Synthesis of (Z)-nitrone 6. Conditions: a) LiAlH₄, THF, 1 h, rt; b) 1. NaIO₄, CH₃CN/H₂O, 1 h, rt; 2...
  
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4. Scheme 3: [3 + 3]-Cyclization of (Z)-nitrone 6 with lithiated allene 9. Conditions: a) n-BuLi, THF, 15 min, −...
  
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5. Scheme 4: Synthesis of 1,2-oxazine 4 by acetal formation from 10. Conditions: a) 1-bromo-4-(dimethoxymethyl)b...
  
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6. Scheme 5: Synthesis of bicyclic ketone 11 by Lewis acid-induced rearrangement and reduction to alcohols 12a a...
  
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7. Scheme 6: Synthesis of bicyclic diols 15 and of trityl-protected bicyclic 1,2-oxazine 16. Conditions: a) SnCl₄...
  
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8. Scheme 7: Hydrogenolyses of bicyclic 1,2-oxazine derivatives 15a and 15b. Conditions: a) H₂, Pd/C, MeOH, EtOA...
  
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9. Scheme 8: Suzuki cross-coupling of 15a leading to biphenyl derivative 18 and hydrogenolysis to 19. Conditions...
  
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10. Scheme 9: Synthesis of N-benzylated p-terphenyl derivative 21 by Suzuki cross-coupling of 12a with 20 and sub...
  
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11. Scheme 10: Attempted reductive cleavage of the N–O bond of compound 21 by samarium diiodide and reaction of 12a...
  
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12. Scheme 11: Deprotection of compound 21 and samarium diiodide-mediated reaction of 26. Conditions: a) TBAF, THF...
  
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13. Scheme 12: Suzuki cross-coupling of compound 16. Conditions: Pd(PPh₃)₂Cl₂, 2 M Na₂CO₃, DMF, 80 °C, 3 d.
  
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14. Scheme 13: Hydrogenolysis of compound 27 and samarium diiodide-mediated reaction leading to compounds 30 and 31...
  
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Beilstein J. Org. Chem. 2014, 10, 1749–1758, doi:10.3762/bjoc.10.182

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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

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Published 25 Aug 2014

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1. Graphical Abstract
2. Figure 1: Previously reported low-valent glycoasterisk α-D-Man ligand based on a persulfurated benzene core [30] ...
  
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3. Scheme 1: Synthesis of trivalent trithiotriazine-based glycoclusters.
  
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4. Scheme 2: Synthesis of mixed triazine-based glycoclusters.
  
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5. Figure 2: Dynamic light scattering experiments of bis-D-galactosyl proparyl cluster 16 with lecA. Distributio...
  
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6. Figure 3: Typical ITC measurements representing the raw ITC data (top) and integrated titration curves (botto...
  
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7. Figure 4: Inhibition of PAO1 biofilm formation by D-galactose cluster 1, L-fucose cluster 14, and D-glucose c...
  
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Beilstein J. Org. Chem. 2014, 10, 1981–1990, doi:10.3762/bjoc.10.206

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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

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Published 19 Sep 2014

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1. Graphical Abstract
2. Scheme 1: Functionalization of carbohydrates; reagents and conditions: (a) In, allyl bromide, EtOH/H₂O, ultra...
  
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3. Scheme 2: Deprotection sequence; reagents and conditions: (a): HCl/MeOH, rt, 16–24 h, then MeOH, CH₂Cl₂, O₃, ...
  
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Beilstein J. Org. Chem. 2014, 10, 2230–2234, doi:10.3762/bjoc.10.231

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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

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Published 22 Sep 2014

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1. Graphical Abstract
2. Scheme 1: Principle of MOE with Ac₄GlcNCyoc (1) and subsequent ligation by a DAinv reaction: The chemically m...
  
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3. Figure 1: Hexosamine derivatives with cyclopropene tags. Cyoc = (2-methylcycloprop-2-en-1-yl)methoxycarbonyl,...
  
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4. Scheme 2: Synthesis of the cyclopropene-modified hexosamine derivatives 1 and 2.
  
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5. Scheme 3: Labeling strategy for metabolically incorporated monosaccharides.
  
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6. Figure 2: Labeling of metabolically engineered cell-surface glycoconjugates. HEK 293T cells were grown for 48...
  
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7. Figure 3: Western blot analysis of soluble glycoproteins. HeLa S3 cells were grown for 48 h with 100 µM cyclo...
  
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Beilstein J. Org. Chem. 2014, 10, 2235–2242, doi:10.3762/bjoc.10.232

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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

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Published 13 Oct 2014

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1. Graphical Abstract
2. Figure 1: Structures of the repeating unit of MenX CPS and synthetic oligomers 1–3.
  
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3. Scheme 1: Reagents and conditions: a) NiCl₂/NaBH₄, MeOH; b) Ac₂O, 86% over 2 steps; c) TBAF, THF, −40 °C to r...
  
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4. Scheme 2: Reagents and conditions: a) PivCl in pyridine, then I₂ in 19:1 pyridine/H₂O, then 1 M TEAB (45%); b...
  
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5. Scheme 3: Reagents and conditions: a) SIDEA, Et₃N, DMSO: 11 (64%), 12 (49%), 13 (51%); b) CRM₁₉₇, 100 mM NaP_i...
  
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6. Figure 2: IgG levels detected at OD = 1 in individual post 3 sera (sera collected two weeks after the third i...
  
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7. Figure 3: A) IgG levels detected at OD = 1 in individual post 3 sera of BALB/c mice immunization at 0.3 μg sa...
  
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Beilstein J. Org. Chem. 2014, 10, 2367–2376, doi:10.3762/bjoc.10.247

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Multivalent glycosystems for nanoscience

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