2-Azidoethoxy derivatives of 2-aminocyclohexanecarboxylic acids (ACHC): interesting building blocks for the synthesis of cyclic \uf062-peptide conjugates

Oligomers of cyclic beta-aminoacids possess a high resistance to peptidase-catalyzed hydrolysis and display a high intrinsic tendency to adopt regular secondary structures. These characteristics are attractive to develop new biologically active substances. However, cyclic-betapeptides often show limited solubility in water and cannot be conjugated to biologically relevant fragments, such as oligosaccharides, which are often essential for full biololgical activity of natural alfapeptides. In this article, we report the synthesis of one trans- and one cis-2-aminocyclohexane carboxylic acid (ACHC) both functionalized with a hydroxy group, to increase the solubility in water, and an azidoethoxy group to allow the synthesis of cyclic-beta-peptide conjugates by a "click reaction

Second generation of Fucose-based DC-SIGN ligands : affinity improvement and specificity versus Langerin

DC-SIGN and Langerin are two C-type lectins involved in the initial steps of HIV infections: the former acts as a viral attachment factor and facilitates viral invasion of the immune system, the latter has a protective effect. Potential antiviral compounds targeted against DC-SIGN were synthesized using a common fucosylamide anchor. Their DC-SIGN affinity was tested by SPR and found to be similar to that of the natural ligand Lewis-X (Le X). The compounds were also found to be selective for DC-SIGN and to interact only weakly with Langerin. These molecules are potentially useful therapeutic tools against sexually transmitted HIV infection