Dendritic scaffolds containing mannose derivatives have been synthesized for their potential use as inhibitors of bacterial infection
An important step in the process of bacterial infection involves the adhesion of the bacteria onto the host tissue. For certain bacteria, this occurs through the binding of their hair-like appendages to mannose sugars on the host's surface. Molecules that contain a mannose residue can, therefore, be used block the binding and inhibit adhesion.
To investigate the design of more efficient and specific inhibitors, René Roy and co-workers at the University of Québec in Montreal have devised1 a synthetic route for making versatile dendritic architectures onto which mannose and other sugars can be easily attached. Their approach uses a coupling reaction between thioacetylated cores and TRIS derivatives to produce a dendritic scaffold. A mannopyranoside — a sugar derivative — is then attached to each branch through a Cu(I)-catalysed cycloaddition reaction. Depending on the choice of reactants used in the scaffold synthesis, dendrimers with either 12 or 18 mannose residues were formed.
The reactions involved were quick, simple and high-yielding. Higher-generation dendritic structures are now being investigated by Roy and co-workers, and biological studies will be undertaken to investigate the therapeutic potential of the various compounds.
References
Chabre, Y. M., Contino-Pépin, C., Placide, V., Shiao, T. C. & Roy, R. Expeditive synthesis of glycodendrimer scaffolds based on versatile TRIS and mannoside derivatives. J. Org. Chem. 10.1021/jo8008935 (2008).
Rights and permissions
About this article
Cite this article
Portman, R. Branching out. Nature Chem (2008). https://doi.org/10.1038/nchem.32
Published:
DOI: https://doi.org/10.1038/nchem.32