Carbohydrate inhibitors of cholera toxin

• Vajinder Kumar and
• W. Bruce Turnbull

Beilstein J. Org. Chem. 2018, 14, 484–498, doi:10.3762/bjoc.14.34

• toxin lectins [72]. Gibson and co-workers made a series of polyacrylates bearing pentafluorophenyl active ester groups which could be subsequently converted to polyacrylamides by reaction with amine linkers of varying lengths [71]. The attachment of galactosyl azides provided a series of glycopolymer

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

• carbohydrate-based drugs. One such example of a therapeutic application can be found in a recent novel approach to treating anti-myelin-associated glycoprotein (anti-MAG) neuropathy, a rare, disabling autoimmune disorder. The use of a multivalent glycopolymer mimicking the natural HNK-1 epitope proved to be a

Probing multivalency in ligand–receptor-mediated adhesion of soft, biomimetic interfaces

• Stephan Schmidt,
• Hanqing Wang,
• Daniel Pussak,
• Simone Mosca and
• Laura Hartmann

Beilstein J. Org. Chem. 2015, 11, 720–729, doi:10.3762/bjoc.11.82

• simply mediated by the high number of ligand–receptor interactions. Keywords: bio-interfaces; cell mimetic; glycocalyx; glycopolymer; molecular recognition; RICM; specific adhesion; Introduction Vast amounts of biological processes are mediated by interactions between membrane proteins and

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

• azobenzene unit allows for the photosensitive control of glycoligand binding to protein receptors. These stimuli-sensitive glycoligands promote the understanding of multivalent binding and will be further developed as novel biosensors. Keywords: azobenzene; glycopolymer; lectin binding; multivalency

The synthesis of well-defined poly(vinylbenzyl chloride)-grafted nanoparticles via RAFT polymerization

• John Moraes,
• Kohji Ohno,
• Guillaume Gody,
• Thomas Maschmeyer and
• Sébastien Perrier

Beilstein J. Org. Chem. 2013, 9, 1226–1234, doi:10.3762/bjoc.9.139

• polymerization (ATRP) [30][31]. It has, therefore, been used in a variety of systems as a precursor to glycopolymer stars [29], photo- and pH-responsive nanoparticles [30], nanofibres [28], comb, graft and star polymers [27], and triblock copolymers [26]. While there have been reports of the (co)polymerization

End-labeled amino terminated monotelechelic glycopolymers generated by ROMP and Cu(I)-catalyzed azide–alkyne cycloaddition

• Ronald Okoth and
• Amit Basu

Beilstein J. Org. Chem. 2013, 9, 608–612, doi:10.3762/bjoc.9.66

• of the NHS esters had indeed been displaced. CuAAC between propargyl β-D-galactoside 10a [23] and azido polymer 9 was achieved in 10 minutes by a microwave-assisted protocol to give galactosyl polymer 11a. We also prepared the mannosylated glycopolymer 11b in a similar manner (see Supporting

• – a and olefinic protons – b. Galactosyl glycopolymer 11a (middle) showing introduction of sugar protons – c and triazole protons – d. Amino-terminated galactosyl glycopolymer 12a (top) showing disappearance of TMS protons. Synthesis of terminating agent 3, ROMP and post ROMP modifications

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

• ]. 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

• diastereomeric (monovalent) C-glycosidic Con A ligands displayed only a small difference in the free energies of binding to Con A, a sizable difference was measured between the corresponding multivalent C-glycosides (calculated per monovalent ligand within the glycopolymer). Such effects can be analyzed in the

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

• . Keywords: click chemistry; con A lectin; dynamic light scattering; glycopolymer; polymer nanoparticles; Introduction Over the last decades, research efforts in pharmaceutical, food and cosmetics technologies have been directed not only towards the syntheses of new bioactive entities or medicines, but also

• glycopolymer. Conclusion Water soluble glycopolymers can easily be prepared by the CuI-catalyzed cycloaddition of an azido mannopyrannoside derivative and a poly(propargyl acrylate-co-N-vinyl pyrrolidone). These glycopolymers can be used as polymer surfactants, in conjunction with another non-ionic triblock

• ) (1.0 g) was dissolved in ethyl acetate (25 mL) under gentle stirring and heating for 2 h (ethyl acetate was added in order to adjust the volume to 25 mL). Pluronic® F-68 and the glycopolymer, dissolved in water (50 mL), were then added to the preceding solution, the mixture stirred for 10 min and then