Porphyrin

Porphyrins are a group of heterocyclic macrocycle organic compounds, composed of four modified pyrrole subunits interconnected at their α carbon atoms via methine bridges (=CH−). The parent porphyrin is porphin, and substituted porphines are called porphyrins. The porphyrin ring structure is aromatic, with a total of 26 electrons in the conjugated system. Various analyses indicate that not all atoms of the ring are involved equally in the conjugation or that the molecule's overall nature is substantially based on several smaller conjugated systems. One result of the large conjugated system is that porphyrin molecules typically have very intense absorption bands in the visible region and may be deeply colored; the name "porphyrin" comes from the Greek word πορφύρα (porphyra), meaning purple.

Many porphyrins are naturally occurring; one of the best-known porphyrins is heme, the pigment in red blood cells, a cofactor of the protein hemoglobin.

Porphyrins are the conjugate acids of ligands that bind metals to form complexes. The metal ion usually has a charge of 2+ or 3+. A schematic equation for these syntheses is shown:

A porphyrin without a metal-ion in its cavity is a free base. Some iron-containing porphyrins are called hemes. Heme-containing proteins, or hemoproteins, are found extensively in nature. Hemoglobin and myoglobin are two O₂-binding proteins that contain iron porphyrins. Various are also hemoproteins.

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