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

• . Substitution of the bromide by azide also proceeded uneventfully (NaN3, DMF, rt, 16 h) to afford intermediate glycodendron 19 in 93% yield. Finally, coupling of the propargylated core 2 with azidodendron 19 under the typical CuAAc conditions gave peracetylated intermediate 20 which was readily deprotected to

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

• divalent glycodendron 3 (Scheme 1). Then, ozonolysis yields the alcohol 4 in a quantitative reaction, which can be further modified at the focal hydroxy group, leading to 5 after allylation and to the primary alcohol 6 in the following ozonolysis step. However, the alcohol 4 can also be employed in another

• etherification reaction with MDC to deliver glycodendron 7 of the next dendron generation. This in turn, can be further elaborated to give the alcohol 8 and the formerly unknown glycodendron alkene 9. Initially, postsynthetic focal point modification of glycodendrons was attempted by direct etherification

• employing long chain alkyl bromides. Williamson etherification of 4 using tetradecanyl bromide led to 10 in only 33% yield, and the same reaction starting with the primary alcohol 6 led to 11 in a somewhat better yield of 44% (Scheme 2). When the tetravalent glycodendron 3 was employed in the same

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

• strategies based on dendritic cells (DCs) armed with specific tumor antigens have been widely exploited due the properties of these immune cells in coordinating an innate and adaptive response. Here, we describe the convergent synthesis of the bifunctional multivalent glycodendron 5, which contains nine

• residues of mannose for DC targeting and one residue of an immunogenic mimetic of a carbohydrate melanoma associated antigen. The immunological assays demonstrated that the glycodendron 5 is able to induce human immature DC activation in terms of a phenotype expression of co-stimulatory molecules

• expression and MHCII. Furthermore, DCs activated by the glycodendron 5 stimulate T lymphocytes to proliferate in a mixed lymphocytes reaction (MLR). Keywords: cancer immunotherapy; DC-SIGN; DC targeting; glycodendron; GM3-lactone mimetic; multivalent glycosystems; multivalent interactions; Introduction