protoporphyrinogen IX
{{Chembox
| verifiedrevid = 439771218
| ImageFile = Protoporphyrinogen IX.svg
| ImageSize = 200 px
| IUPACName =
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 7412-77-3
| ChEBI = 57307
| ChemSpiderID = 20171538
| PubChem = 20849104
| StdInChI=1S/C34H40N4O4/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25/h7-8,35-38H,1-2,9-16H2,3-6H3,(H,39,40)(H,41,42)/p-2
| StdInChIKey = UHSGPDMIQQYNAX-UHFFFAOYSA-L
| SMILES = CC1=C2CC3=C(C(=C(N3)CC4=C(C(=C(N4)CC5=C(C(=C(N5)CC(=C1CCC(=O)[O-])N2)CCC(=O)[O-])C)C=C)C)C=C)C
| MeSHName = protoporphyrinogen
}}
|Section2={{Chembox Properties
| Formula = C34H38N4O4
| MolarMass = 566.7 g/mol
| Appearance =
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|Section3={{Chembox Hazards
| MainHazards =
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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.
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|reason=Source?|date=December 2021}}
Biosynthesis
The compound is synthesized in most organisms from coproporphyrinogen III by the enzyme coproporphyrinogen oxidase:
File: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.{{cite encyclopedia|chapter=Hemes in Biology|author=Paul R. Ortiz de Montellano|year=2008|encyclopedia=Wiley Encyclopedia of Chemical Biology|pages=1–10 |doi=10.1002/9780470048672.wecb221|publisher=John Wiley & Sons|isbn=978-0470048672}}
References
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See also
{{Tetrapyrroles}}
{{Heme metabolism intermediates}}
{{DEFAULTSORT:Protoporphyrinogen Ix}}
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