Peptide Multifunctionalization via Modular Construction of Trans-ABC Porphyrin on Resin.

Peptide multifunctionalization is a crucial technique to develop peptide-based agents for various purposes. Porphyrin-peptide conjugates are a class of popular multifunctional peptides renowned for their multifunctional and multimodal properties. However, the tedious synthetic works for porphyrin building blocks are involved in most previous studies. In this work, a modular solid-phase synthetic approach is reported to construct trans-ABC porphyrin on peptide chains without presynthesized porphyrin building blocks. The products from this approach, which inherit both functionalities from the porphyrins and the modules employed for constructing porphyrins, show potential in biomedical and biomaterial applications. Furthermore, by extending this synthetic approach, the first example of "resin-to-resin" reaction is reported to link two peptides together along the construction of porphyrin motifs to give porphyrin-peptide conjugates with two different peptide chains.