Glycodendrimers: tools to explore multivalent galectin-1 interactions

• Jonathan M. Cousin and
• Mary J. Cloninger

Beilstein J. Org. Chem. 2015, 11, 739–747, doi:10.3762/bjoc.11.84

• ][25]. Synthetic multivalent ligands have been observed to enhance galectin-1 binding through the glycoside cluster effect by mediating the formation of cross-linked aggregates [26][27][28]. Tinari et al. observed galectin-1 augmentation of homotypic cellular aggregation in human melanoma cells (A375

Synthesis of enantiopure sugar-decorated six-armed triptycene derivatives

• Paola Bonaccorsi,
• Maria Luisa Di Gioia,
• Antonella Leggio,
• Lucio Minuti,
• Teresa Papalia,
• Carlo Siciliano,
• Andrea Temperini and
• Anna Barattucci

Beilstein J. Org. Chem. 2013, 9, 2410–2416, doi:10.3762/bjoc.9.278

• cluster effect [7][8][9][10][11]. These glycoconjugates showed their potentialities not only in the interpretation of molecular recognition events but also in biotechnological, pharmaceutical and medical fields [12]. Our research interest is focused on the synthesis of new glycoconjugates and the study of

Low-generation dendrimers with a calixarene core and based on a chiral C₂-symmetric pyrrolidine as iminosugar mimics

• Marco Marradi,
• Stefano Cicchi,
• Francesco Sansone,
• Alessandro Casnati and
• Andrea Goti

Beilstein J. Org. Chem. 2012, 8, 951–957, doi:10.3762/bjoc.8.107

• [14]. Multivalent calixarenes functionalised with carbohydrate units (glycocalixarenes) [15] have been extensively reported in the literature and represent examples of sugar clustering on macrocyclic structures [16][17]. Thanks to the “glycoside cluster effect” [18][19][20], glycocalixarenes can

High-affinity multivalent wheat germ agglutinin ligands by one-pot click reaction

• Henning S. G. Beckmann,
• Heiko M. Möller and
• Valentin Wittmann

Beilstein J. Org. Chem. 2012, 8, 819–826, doi:10.3762/bjoc.8.91

• ; cluster effect; lectins; multivalency; Introduction The recognition of carbohydrate structures by carbohydrate binding proteins (lectins) plays a fundamental role in numerous intra- and intercellular events during development, inflammation, immune response, cancer metastasis, and pathogen–host

• ligands for the Shiga-like [14][15] and cholera toxins [16][17] both belonging to the AB5 family of bacterial toxins. The frequent observation that the binding affinity of a multivalent ligand increases exponentially with the number of binding sites has been termed the glycoside cluster effect [18][19

• ]. Due to the exponential increase of binding affinities, the cluster effect often leads to the amplification of the binding selectivity. This was experimentally demonstrated, for example, by Mortell et al. while investigating glycopolymer ligands of concanavalin A (Con A) [20]. Whereas two

Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations

• Baptiste Thomas,
• Michele Fiore,
• Isabelle Bossu,
• Pascal Dumy and
• Olivier Renaudet

Beilstein J. Org. Chem. 2012, 8, 421–427, doi:10.3762/bjoc.8.47

• viruses or bacteria [2][3][4][5]. In a suitable density and spatial display, clusters of carbohydrate indeed allow multiple contacts with a target protein, thus increasing avidity by means of the “glycoside cluster effect” [6][7]. While the recent progress in glycomics has led to the design of

New amphiphilic glycopolymers by click functionalization of random copolymers – application to the colloidal stabilisation of polymer nanoparticles and their interaction with concanavalin A lectin

• Otman Otman,
• Paul Boullanger,
• Eric Drockenmuller and
• Thierry Hamaide

Beilstein J. Org. Chem. 2010, 6, No. 58, doi:10.3762/bjoc.6.58

• the cluster effect [19][20]. The lectin–carbohydrate specificity strongly depends on the lectin. Several of these are very sensitive to the nature of the carbohydrate (e.g. Man vs Gal), whereas others are more sensitive to the orientation of the anomeric substituent (i.e. α vs β). Concanavalin A, used