Linking applicatory functions to the 3-position of pyrrole by click chemistry

Abstract

A straight forward and reliable method was developed to tether recognition functions to a side chain in position 3 of pyrroles via triazole linkage. The products are precursors for functionalized polypyrroles, e. g. for coating magnetic nanoparticles or selective electrodes. A pyrrole with an azido function located at the terminus of a side chain in position 3 was submitted to coppercatalyzed Meldal-Sharpless click reaction with alkynes bearing biotin, nitrilotriacetic acid or a RGD-containing cyclopentapeptide. The latter presents a very versatile building block for the introduction of the RGD-moiety in a variety of potential substrates.