Modern aspects of the Chemistry of protoporphyrin IX

The Red Color of Life Transformed – Synthetic Advances and Emerging Applications of Protoporphyrin IX in Chemical Biology

“…The interest in PPIX has led to the development of a range of functionalization reactions for the vinyl groups and propionic acid moieties, the majority of whom has been discussed in a comprehensive review by Pavlov . A selection of frequently applied functionalization reactions for PPIX ( 2 ), PPIX‐dme ( 3 ) and their metal complexes, is given in Scheme .…”

“…Nevertheless, the natural abundance of heme in hemoglobin enables the isolation of PPIX from blood in significant amounts, which results in the commercial availability of PPIX and several PPIX metal complexes. For this reason, synthetic efforts have mostly been focused on the modification of the periphery of PPIX …”

“…Currently, it is widely studied in biomedicine for applications such as photodynamic therapy (PDT), antimicrobial and antiviral phototherapy, biosensing, bioimaging, catalysis and interference with biochemical pathways . Additionally, the inherent properties of PPIX as a porphyrin, the wide range of biological functions manifested in nature through manipulation of the macrocycle conformation, its ready availability and the possibility of facile attachment of groups at its propionate moieties renders it a compound frequently employed for a variety of other applications such as sensing, light harvesting, electrochemistry as well as uses in supramolecular chemistry which have been reviewed here by Bhosale et al…”

Supramolecular Chemistry of Protoporphyrin IX and Its Derivatives

“…[10] A number of protocols for the synthesis and functionalisation of PP-IX derivatives have been reported; [8] however, the method developed by Martin and co-workers enables the synthesis of PP-IX on a large scale by the MacDonald condensation method (Scheme 2). Possible chemical transformations of the vinyl group, for example, could be reduction, oxidation, addition, substitution, elimination, electrocyclic reactions and olefin metathesis.…”

“…In this section we give a brief summary of recent developments in PP-IX synthesis, taking account of publications not covered by earlier synthetic reviews. [10] A number of protocols for the synthesis and functionalisation of PP-IX derivatives have been reported; [8] however, the method developed by Martin and co-workers enables the synthesis of PP-IX on a large scale by the MacDonald condensation method (Scheme 2). [11] In 2001, Velasco's group described a new method for the functionalisation of PP-IX derivative 8 (Scheme 3) at its vinyl groups by means of the Heck reaction.…”