| Abstract
| - The present work describes synthetic concepts for the coupling of peptides to polyphenylene dendrimers(PPDs). Novel functionalized cyclopentadienones have been synthesized whose Diels−Alder cycloaddition with various core molecules leads to polyphenylene dendrimers possessing (protected) aminoor carboxyl groups. In addition, the resulting functionalized molecules exhibit the characteristic shape-persistence and monodispersity of PPDs. Their functions have been used for the attachment ofpolylysine to the dendritic scaffold. Three different methods for the decoration of dendrimers withpolypeptides are presented. First, polylysine segments are grafted from the surface of the dendrimersemploying α-amino acid N-carboxyanhydride (NCA) polymerization. Second, the C-terminal carboxylgroups of protected polypeptides are activated and then coupled to the amino groups on the surfaceof the PPD. Finally, cysteine terminated, unprotected peptide sequences are attached to polyphenylenedendrimers utilizing the addition of the sulfhydryl group of a cysteine to the maleimide functions onthe dendrimer surface. Moreover, Diels−Alder cycloaddition of suitably functionalized cyclopentadienons to a desymmetized core molecule allows the design of a dendritic scaffold with a specific numberof different anchor groups on its periphery. These approaches are important for the tailoring of new,shape-persistent, polyfunctional multiple antigen conjugates.
|
