Coproporphyrinogen III: Difference between revisions
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The compound is a [[porphyrinogen]], a class of compounds characterized by a [[hexahydroporphine]] core with various [[side chain]]s. The [[coproporphyrinogen]]s have the outermost [[hydrogen]] atoms of the core replaced by four [[methyl]] groups {{chem2|\sCH3}} (M) and four [[propionic acid]] groups {{chem2|\sCH2\sCH2\sCOOH}} (P). In coproporphyrogen III, the order around the outer ring is MP-MP-MP-PM. For comparison, [[coproporphyrinogen I]] has them in the sequence MP-MP-MP-MP. [[heme]]. |
The compound is a [[porphyrinogen]], a class of compounds characterized by a [[hexahydroporphine]] core with various [[side chain]]s. The [[coproporphyrinogen]]s have the outermost [[hydrogen]] atoms of the core replaced by four [[methyl]] groups {{chem2|\sCH3}} (M) and four [[propionic acid]] groups {{chem2|\sCH2\sCH2\sCOOH}} (P). In coproporphyrogen III, the order around the outer ring is MP-MP-MP-PM. For comparison, [[coproporphyrinogen I]] has them in the sequence MP-MP-MP-MP. [[heme]]. |
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==Biosynthesis== |
==Biosynthesis and metabolism== |
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In the main [[porphyrin |
In the main [[porphyrin biosynthesis]] pathway, coproporphyrinogen III is derived from [[uroporphyrinogen III]] by the action of the enzyme [[uroporphyrinogen III decarboxylase]]: |
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[[File:Coproporphyrinogen-III-synthesis-from-uroporphyrinogen-III.png|center|480px|alt=Biosynthesis of coproporphyrinogen-III from uroporphyrinogen-III]] |
[[File:Coproporphyrinogen-III-synthesis-from-uroporphyrinogen-III.png|center|480px|alt=Biosynthesis of coproporphyrinogen-III from uroporphyrinogen-III]] |
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The conversion entails four [[decarboxylation]]s, which turn the four acetic acid groups {{chem2|\sCH2\sCOOH}} into methyl groups {{chem2|\sCH3}}, with release of four [[carbon dioxide]] molecules.<ref name=Hemes>{{cite encyclopedia|title=Hemes in Biology|author=Paul R. Ortiz de Montellano|year=2008|encyclopedia=Wiley Encyclopedia of Chemical Biology|doi=10.1002/9780470048672.wecb221|publisher=John Wiley & Sons}}</ref> |
The conversion entails four [[decarboxylation]]s, which turn the four acetic acid groups {{chem2|\sCH2\sCOOH}} into methyl groups {{chem2|\sCH3}}, with release of four [[carbon dioxide]] molecules.<ref name=Hemes>{{cite encyclopedia|title=Hemes in Biology|author=Paul R. Ortiz de Montellano|year=2008|encyclopedia=Wiley Encyclopedia of Chemical Biology|doi=10.1002/9780470048672.wecb221|publisher=John Wiley & Sons}}</ref> |
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Revision as of 22:18, 10 March 2019
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| 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 many compounds that are critical for living organisms, such as hemoglobin and chlorophyll. It is a colorless solid.
The compound is a porphyrinogen, a class of compounds characterized by a hexahydroporphine core with various side chains. The coproporphyrinogens have the outermost hydrogen atoms of the core replaced by four methyl groups −CH3 (M) and four propionic acid groups −CH2−CH2−COOH (P). In coproporphyrogen III, the order around the outer ring is MP-MP-MP-PM. For comparison, coproporphyrinogen I has them in the sequence MP-MP-MP-MP. heme.
Biosynthesis and metabolism
In the main porphyrin biosynthesis pathway, coproporphyrinogen III is derived from uroporphyrinogen III by the action of the enzyme uroporphyrinogen III decarboxylase:
The conversion entails four decarboxylations, which turn the four acetic acid groups −CH2−COOH into methyl groups −CH3, with release of four carbon dioxide molecules.[1]
Coproporphyrinogen III is further used as a substrate for the enzyme coproporphyrinogen III oxidase which oxidizes and further decarboxylates it to protoporphyrinogen IX.
References
- ^ 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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