Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside

• Dimitri Fayolle,
• Nathalie Berthet,
• Bastien Doumeche,
• Olivier Renaudet,
• Peter Strazewski and
• Michele Fiore

Beilstein J. Org. Chem. 2019, 15, 937–946, doi:10.3762/bjoc.15.90

• compounds similar to other efficient multivalent glycoconjugates obtained by TEC of sugar thiols with different multivalent scaffolds such as octasilsesquioxanes [35], cyclopeptides [36][37] and polymers [38]. Both compounds 5 and 8 showed low IC50 values (a tenth to some hundreds of micromolars) where the

Synthesis of carbohydrate-scaffolded thymine glycoconjugates to organize multivalency

• Anna K. Ciuk and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2015, 11, 668–674, doi:10.3762/bjoc.11.75

• on the cell surface. Thus many synthetic multivalent glycoconjugates have been developed as important tools for glycobiological research. We are expanding this collection of molecules by the introduction of carbohydrate-scaffolded divalent glycothymine derivatives that can be intramolecularily

• Information File 1). Conclusion In line with our former work on the orientational control of carbohydrate ligands assembled on a surface [6], we seeked the synthesis of multivalent glycoconjugates that allow the organization of multivalency. To start this new approach, we have introduced a divalent

Multivalent glycosystems for nanoscience

• Thisbe K. Lindhorst

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

• the field of glycosciences. This enterprise has focused its research on the potential applications and social benefits that lie in the field. For instance, multivalent glycoconjugates can be used as anti-adhesive drugs against microbial infections. They could be developed into bioimaging agents that

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

• understand these phenomena, dendrimers and dendrons have been developed to provide multivalent glycoconjugates [13][14]. Here, we propose the synthesis of novel dendron structures which allow for the multivalent conjugation of carbohydrates via carbonyl chemistry. Results and Discussion The

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

• carbohydrate–protein interactions are complex mechanisms that play key roles in biology [1]. To decipher, exploit or inhibit these recognition processes, a large variety of synthetic multivalent glycoconjugates have been developed over the last decade [2][3][4]. For a long time, these structures have

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

• Thisbe K. Lindhorst Katharina Elsner Otto Diels Institute of Organic Chemistry, Christiana Albertina University of Kiel, Otto-Hahn-Platz 3–4, D-24098 Kiel 10.3762/bjoc.10.152 Abstract Glycodendrons are multivalent glycoconjugates bearing an orthogonal functional group at the focal point of the

• etherification, thiol-ene reaction and in particular olefin cross metathesis. Keywords: amphiphilic glycomimetics; cross metathesis; glycodendrons; multivalent glycoconjugates; multivalent glycosystems; Introduction In addition to nucleic acids and proteins, molecular life is based on a third important class

• frequently applied for the synthesis of multivalent glycoconjugates [6]. Dendrons resemble a branched fragment of a whole dendrimer with an orthogonal functional group (FG) at the focal point of the molecular fragment (Figure 1a). This molecular architecture comprises the possibility to anchor a multivalent