Protoporphyrinogen IX

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Protoporphyrinogen IX
Protoporphyrinogen IX.svg
Identifiers
MeSH protoporphyrinogen
PubChem CID
Properties
C34H38N4O4
Molar mass 566.7 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Protoporphyrinogen IX is an organic chemical compound which is produced along the synthesis of porphyrins, a class of critical biochemicals that include hemoglobin and chlorophyll. It is a direct precursor of protoporphyrin IX.

Contents

The compound is a porphyrinogen, meaning that it has a non-aromatic hexahydroporphine core, which will be oxidized to a porphine core in later stages of the heme synthesis. Like most porphyrinogens, it is colorless.[ citation needed ]

Biosynthesis

The compound is synthesized in most organisms from coproporphyrinogen III by the enzyme coproporphyrinogen oxidase:

Proptoporphyrinogen-IX-synthesis-from-coproporphyrinogen-III.png

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 IX is later converted into protoporphyrin IX, the first colored tetrapyrrole in the biosynthesis of hemes. [1]

Related Research Articles

Heme Chemical coordination complex of an iron ion chelated to a porphyrin

Heme, or haem, is a precursor to hemoglobin, which is necessary to bind oxygen in the bloodstream. Heme is biosynthesized in both the bone marrow and the liver.

Protoporphyrinogen oxidase

Protoporphyrinogen oxidase or protox is an enzyme that in humans is encoded by the PPOX gene.

Porphine Chemical compound

Porphine or porphin is an organic chemical compound with formula C20H14N4. The molecule consists of four pyrrole-like rings joined by four methine (=CH−) groups to form a larger macrocycle ring, which makes it the simplest of the tetrapyrroles. It is an aromatic and heterocyclic compound, solid at room temperature.

Coproporphyrinogen III oxidase

Coproporphyrinogen-III oxidase, mitochondrial is an enzyme that in humans is encoded by the CPOX gene. A genetic defect in the enzyme results in a reduced production of heme in animals. The medical condition associated with this enzyme defect is called hereditary coproporphyria.

Coproporphyrinogens are tetrapyrroles with four propionic acid groups and an equal number of substituted methyls.

Coproporphyrinogen III Chemical compound

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.

Uroporphyrinogen III Chemical compound

Uroporphyrinogen III is a tetrapyrrole, the first macrocyclic intermediate in the biosynthesis of heme, chlorophyll, vitamin B12, and siroheme. It is a colorless compound, like other porphyrinogens.

Hydroxymethylbilane Chemical compound

Hydroxymethylbilane, also known as preuroporphyrinogen, is an organic compound that occurs in living organisms during the synthesis of porphyrins, a group of critical substances that include haemoglobin, myoglobin, and chlorophyll. The name is often abbreviated as HMB.

Protoporphyrin IX chemical compound

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 soluble in water. The name is often abbreviated as PPIX.

Uroporphyrinogen I Chemical compound

Uroporphyrinogen I is an isomer of uroporphyrinogen III, a metabolic intermediate in the biosynthesis of heme. A type of porphyria is caused by production of uroporphyrinogen I instead of III.

Coproporphyrinogen I Chemical compound

Coproporphyrinogen I is an isomer of coproporphyrinogen III, a metabolic intermediate in the normal biosynthesis of heme. The compound is not normally produced by the human body; its production and accumulation causes a type of porphyria.

In enzymology, a coproporphyrinogen dehydrogenase (EC 1.3.99.22) is an enzyme that catalyzes the chemical reaction

Protoporphyrinogen IX dehydrogenase (menaquinone) is an enzyme with systematic name protoporphyrinogen IX:menaquinone oxidoreductase. This enzyme catalyses the following chemical reaction

Bifenox Chemical compound

Bifenox is the ISO common name for an organic compound used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase which is necessary for chlorophyll synthesis.

Porphyrinogen

In biochemistry a porphyrinogen is a member of a class of naturally occurring compounds with a tetrapyrrole core, a macrocycle of four pyrrole rings connected by four methylene bridges. They can be viewed as derived from the parent compound hexahydroporphine by the substitution of various functional groups for hydrogen atoms in the outermost (20-carbon) ring.

Chlorophyllide Chemical compound

Chlorophyllide a and Chlorophyllide b are the biosynthetic precursors of chlorophyll a and chlorophyll b respectively. Their propionic acid groups are converted to phytyl esters by the enzyme chlorophyll synthase in the final step of the pathway. Thus the main interest in these chemical compounds has been in the study of chlorophyll biosynthesis in plants, algae and cyanobacteria. Chlorophyllide a is also an intermediate in the biosynthesis of bacteriochlorophylls.

Hexahydroporphine Chemical compound

Hexahydroporphine is an organic chemical compound with formula C20H20N4. The molecule consists of four pyrrole rings connected by methylene bridges −CH2 into a larger (non-aromatic) macrocycle ring, which makes it one of the simplest tetrapyrroles, and the simplest "true" one. As indicated by the name, it may be viewed as derived from porphine by the addition of six hydrogen atoms: four on the methine bridges, and two on the nitrogen atoms.

Fomesafen Herbicide

Fomesafen is the ISO common name for an organic compound used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase which is necessary for chlorophyll synthesis. Soybeans naturally have a high tolerance to fomesafen, via metabolic disposal by glutathione S-transferase. As a result, soy is the most common crop treated with fomesafen, followed by other beans and a few other crop types. It is not safe for maize/corn or other Poaceae.

Butafenacil Chemical compound

Butafenacil is the ISO common name for an organic compound of the pyrimidinedione chemical class used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase to control broadleaf and some grass weeds in crops including cereals and canola.

Aclonifen Chemical compound

Aclonifen is a diphenyl ether herbicide which has been used in agriculture since the 1980s. Its mode of action has been uncertain, with evidence suggesting it might interfere with carotenoid biosynthesis or inhibit the enzyme protoporphyrinogen oxidase (PPO). Both mechanisms could result in the observed whole-plant effect of bleaching and the compound includes chemical features that are known to result in PPO effects, as seen with acifluorfen, for example. In 2020, further research revealed that aclonifen has a different and novel mode of action, targeting solanesyl diphosphate synthase which would also cause bleaching.

References

  1. Paul R. Ortiz de Montellano (2008). "Hemes in Biology". Wiley Encyclopedia of Chemical Biology. John Wiley & Sons. doi:10.1002/9780470048672.wecb221. ISBN   978-0470048672.

See also