Coproporphyrinogen III

Coproporphyrinogen III
Names
IUPAC name
3-[8,12,17-tris(2-carboxyethyl)-3,7,13,18-tetramethyl-5,10,15,20,21,22, 23,24-octahydroporphyrin-2-yl]propanoic acid
Identifiers
3D model (JSmol)
ChemSpider
MeSH Coproporphyrinogen+III
Properties
C36H44N4O8 protonated carboxylic acids
Molar mass 660.757 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

Coproporphyrinogen III is a metabolic intermediate in the biosynthesis of heme. It is a colorless compound, classified as a porphyrinogen.

Biosynthetic context

The tetrapyrrole hydroxymethylbilane is converted by the action of uroporphyrinogen-III synthase to uroporphyrinogen III.[1] Uroporphyrinogen III is subsequently converted into coproporphyrinogen III, a conversion that entails four decarboxylations:

uroporphyrinogen III → coproporphyrinogen III + 4 CO2

Coproporphyrinogen III is further used as a substrate for the enzyme coproporphyrinogen III oxidase which oxidizes and decarboxylates it to protoporphyrinogen IX.

Structural patterns of isomers

The difference between coproporphyrinogen I and III is the arrangements of the four carboxyethyl ("P" groups) and the four methyl groups ("Me" groups). Coproporphyrinogen I has the sequence MeP-MeP-MeP-MeP, whereas in coproporphyrinogen III one MeP-group is reversed and hence an MeP-MeP-MeP-PMe arrangement.

References

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