Protoporphyrinogen IX is an

organic chemical compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon chemical bond, bonds. Due to carbon's ability to Catenation, catenate (form chains with other carbon atoms), millions of organic c ...

which is produced along the synthesis of

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 of porphyrin is porphine, a rare chemical com ...

s, a class of critical biochemicals that include

hemoglobin Hemoglobin (haemoglobin BrE) (from the Greek word αἷμα, ''haîma'' 'blood' + Latin ''globus'' 'ball, sphere' + ''-in'') (), abbreviated Hb or Hgb, is the iron-containing oxygen-transport metalloprotein present in red blood cells (erythrocyte ...

and

chlorophyll Chlorophyll (also chlorophyl) is any of several related green pigments found in cyanobacteria and in the chloroplasts of algae and plants. Its name is derived from the Greek words , ("pale green") and , ("leaf"). Chlorophyll allow plants to a ...

. It is a direct precursor of

protoporphyrin IX Protoporphyrin IX is an organic compound, classified as a porphyrin, that plays an important role in living organisms as a precursor to other critical compounds like heme (hemoglobin) and chlorophyll. It is a deeply colored solid that is not sol ...

. The compound is a

porphyrinogen In biochemistry a porphyrinogen is a member of a class of naturally occurring compounds with a tetrapyrrole core, a macrocycle Macrocycles are often described as molecules and ions containing a ring of twelve or more atoms. Classical examples in ...

, meaning that it has a non-

aromatic In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...

hexahydroporphine Hexahydroporphine is an organic chemical compound with formula . The molecule consists of four pyrrole rings connected by methylene bridges into a larger (non-aromatic) macrocycle ring, which makes it one of the simplest tetrapyrroles, and the ...

core, which will be

oxidized Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a ...

to a

porphine Porphine or porphin is an organic chemical compound with formula . The molecule, which is flat, consists of four pyrrole-like rings joined by four methine (= C H−) groups to form a larger macrocycle ring, which makes it the simplest of the t ...

core in later stages of the heme synthesis. Like most porphyrinogens, it is colorless.

Biosynthesis

The compound is synthesized in most organisms from

coproporphyrinogen III Coproporphyrinogen III is a metabolic intermediate in the biosynthesis of many compounds that are critical for living organisms, such as hemoglobin and chlorophyll. It is a colorless solid. The compound is a porphyrinogen, a class of compounds ...

by the enzyme coproporphyrinogen oxidase: Proptoporphyrinogen-IX-synthesis-from-coproporphyrinogen-III

The process entails conversion of two of four propionic acid groups to vinyl groups. In coproporphyrinogen III, the substituents on the pyrrole rings have the arrangement MP-MP-MP-PM, where M and P are methyl and propionic acid, respectively. In protoporphyrinogen IX, the sequence becomes MV-MV-MP-PM, where V is vinyl. By the action of

protoporphyrinogen oxidase Protoporphyrinogen oxidase or protox is an enzyme that in humans is encoded by the ''PPOX'' gene. Protoporphyrinogen oxidase is responsible for the seventh step in biosynthesis of protoporphyrin IX. This porphyrin is the precursor to hemoglobin, ...

, protoporphyrinogen IX is later converted into

, the first colored tetrapyrrole in the biosynthesis of hemes.

Biosynthesis

References

See also