View source for Chemistry:Coproporphyrinogen I

{{chembox
| ImageFile=Coproporphyrinogen I.svg
| ImageSize=
| IUPACName=3-[7,12,17-tris(2-carboxyethyl)-3,8,13,18-tetramethyl-5,10,15,20,21,22,
23,24-octahydroporphyrin-2-yl]propanoic acid
| OtherNames=
|Section1={{Chembox Identifiers
| ChemSpiderID = 389645
| InChI = 1/C36H44N4O8/c1-17-21(5-9-33(41)42)29-14-26-19(3)23(7-11-35(45)46)31(39-26)16-28-20(4)24(8-12-36(47)48)32(40-28)15-27-18(2)22(6-10-34(43)44)30(38-27)13-25(17)37-29/h37-40H,5-16H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48)
| InChIKey = WIUGGJKHYQIGNH-UHFFFAOYAR
| CASNo = 31110-56-2
| PubChem=440776
| SMILES = O=C(O)CCc1c(c5[nH]c1Cc2[nH]c(c(c2C)CCC(=O)O)Cc3c(c(c([nH]3)Cc4c(c(c([nH]4)C5)CCC(=O)O)C)CCC(=O)O)C)C
| MeSHName=
  }}
|Section2={{Chembox Properties
| Formula=C<sub>36</sub>H<sub>44</sub>N<sub>4</sub>O<sub>8</sub>
| MolarMass=660.757 g/mol
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
  }}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
  }}
}}
'''Coproporphyrinogen I''' is an isomer of [[Chemistry:Coproporphyrinogen III|coproporphyrinogen III]], a [[Biology:Metabolic intermediate|metabolic intermediate]] in the normal [[Biology:Biosynthesis|biosynthesis]] of [[Biology:Heme|heme]]. The compound is not normally produced by the human body; its production and accumulation causes a type of [[Medicine:Porphyria|porphyria]]. <ref name=sassa>S. Sassa  and A. Kappas (2000): "Molecular aspects of the inherited porphyrias". ''Journal of Internal Medicine'', volume 247, issue 2, pages 169-178. {{doi|10.1046/j.1365-2796.2000.00618.x}}</ref>

The difference between coproporphyrinogen I and III is the arrangements of the four [[Chemistry:Propionic acid|carboxyethyl]] ("P" groups) and the four methyl groups ("M" groups).  The I isomer has the sequence MP-MP-MP-MP, whereas in the III isomer it is MP-MP-MP-PM, with the last two side chains reversed.

==Biosynthesys==
Coproporphyrinogen I is not produced in the normal porphyrin biosynthesis pathway. However, if the [[Biology:Enzyme|enzyme]] uroporphyrinogen-III cosynthaseis missing or inactive, the compound [[Chemistry:Uroporphyrinogen I|uroporphyrinogen I]] is produced instead of [[Chemistry:Uroporphyrinogen III|uroporphyrinogen III]]. The enzyme [[Biology:Uroporphyrinogen III decarboxylase|uroporphyrinogen III decarboxylase]] will also act on the I isomer, producing coproporphyrinogen I:<ref name=Hemes>{{cite encyclopedia|chapter=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|isbn=978-0470048672}}</ref><ref name=sassa/>

[[File:Coproporphyrinogen I synthesis from uroporphyrinogen I.png|center|500px]]

The reaction entails the conversion of the four [[Chemistry:Acetic acid|carboxymethyl]] ([[Chemistry:Acetic acid|acetic acid]]) side chains to [[Chemistry:Methyl group|methyl group]]s, with release of four molecules of [[Chemistry:Carbon dioxide|carbon dioxide]].

Unlike the III isomer, coproporphyrinogen I (which is [[Biology:Cytotoxicity|cytotoxic]]) is not further processed by the body, and accumulates. This situation occurs in the [[Biology:Pathology|pathological condition]] called congenital erythropoietic porphyria.<ref name=sassa/>

==References==
<references />

{{Tetrapyrroles}}

[[Category:Tetrapyrroles]]

{{Sourceattribution|Coproporphyrinogen I}}