Protoporphyrinogen IX

Protoporphyrinogen IX

Identifiers
CAS Number	7412-77-3  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:57307
ChemSpider	20171538
MeSH	protoporphyrinogen
PubChem CID	20849104
CompTox Dashboard (EPA)	DTXSID90225068
InChI InChI=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 Key: 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
Properties
Chemical formula	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). Y  verify  (what is  YN ?) 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.

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:

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]

References

1. Paul R. Ortiz de Montellano (2008). "Hemes in Biology". Wiley Encyclopedia of Chemical Biology. John Wiley & Sons. pp. 1–10. doi:10.1002/9780470048672.wecb221. ISBN   978-0470048672.

See also

• Protoporphyrinogen oxidase