Porphyrin

From Proteopedia

Porphyrins are a macrocyclic compounds containing four pyrole rings. Can you identify them in the scene to the right? ) The four pyrole rings are connected together by four . Porphyrins are distinguished from each other by the substituents attached to the pyrole rings. Can you identify the pyrole substituents on this porphyrin (protoporphyrin IX)? They are , and groups. An important function of porphyrins is to form by complexing Fe²⁺ or Fe³⁺ with the lone pairs of electrons on the four nitrogens. Heme displayed as . Since Fe²⁺ and Fe³⁺ prefer to complex with six ligands, there are two positions open for nucleophilic groups to bond whenever the heme associates with a protein. Both of these groups may be residues of a protein, or one of them may be a small substrate molecule. In one of these two ways the heme becomes covalently connected to the protein, and therefore can be called a prosthetic group. Residues that are commonly found as the fifth or sixth ligands are His, Cys and Met. Examples of the fifth ligand being His and the sixth ligand being a small molecule are oxymyoglobin and oxyhemoglobin.