Coproporphyrinogen III: Difference between revisions
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| Formula=C<sub>36</sub>H<sub>44</sub>N<sub>4</sub>O<sub>8</sub> |
| Formula=C<sub>36</sub>H<sub>44</sub>N<sub>4</sub>O<sub>8</sub> |
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| Formula_Comment = protonated carboxylic acids |
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| MolarMass=660.757 g/mol |
| MolarMass=660.757 g/mol |
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| Appearance= |
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Revision as of 15:36, 4 August 2018
Names | |
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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
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
MeSH | Coproporphyrinogen+III |
PubChem CID
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CompTox Dashboard (EPA)
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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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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
- ^ Paul R. Ortiz de Montellano (2008). "Hemes in Biology". Wiley Encyclopedia of Chemical Biology. John Wiley & Sons. doi:10.1002/9780470048672.wecb221.