Coproporphyrinogen III: Difference between revisions

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
CAS Number	2624-63-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	315 ;
MeSH	Coproporphyrinogen+III
PubChem CID	321;
CompTox Dashboard (EPA)	DTXSID40180875 ;
	InChI InChI=1S/C36H44N4O8/c1-17-21(5-9-33(41)42)29-14-27-19(3)22(6-10-34(43)44)30(39-27)15-28-20(4)24(8-12-36(47)48)32(40-28)16-31-23(7-11-35(45)46)18(2)26(38-31)13-25(17)37-29/h37-40H,5-16H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48) Key: NIUVHXTXUXOFEB-UHFFFAOYSA-N ; InChI=1/C36H44N4O8/c1-17-21(5-9-33(41)42)29-14-27-19(3)22(6-10-34(43)44)30(39-27)15-28-20(4)24(8-12-36(47)48)32(40-28)16-31-23(7-11-35(45)46)18(2)26(38-31)13-25(17)37-29/h37-40H,5-16H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48) Key: NIUVHXTXUXOFEB-UHFFFAOYAI;
	SMILES Cc1c2[nH]c(c1CCC(=O)O)Cc3c(c(c([nH]3)Cc4c(c(c([nH]4)Cc5c(c(c([nH]5)C2)C)CCC(=O)O)CCC(=O)O)C)CCC(=O)O)C;
Properties
Chemical formula	C36H44N4O8
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). verify (what is ?) Infobox references

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

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

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.

Heme synthesis—note that some reactions occur in the cytoplasm and some in the mitochondrion (yellow)

This biochemistry article is a stub. You can help Wikipedia by expanding it.

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

[1]

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-'''Coproporphyrinogen III''' in an intermediate in the biosynthesis of natural [[porphyrin]]s.  It is produced from [[uroporphyrinogen III]] by the enzyme [[uroporphyrinogen III decarboxylase]]. In this process, four carboxymethyl groups (-CH<sub>2</sub>CO<sub>2</sub>H) are converted to methyl groups (CH<sub>3</sub>).
+'''Coproporphyrinogen III''' is a [[metabolic intermediate]] in the [[biosynthesis]] of [[heme]]. It is a colorless compound, classified as a [[tetrapyrrole]].
+==Biosynthetic context==
-Subsequently [[coproporphyrinogen III oxidase]] converts coproporphyrinogen III into [[protoporphyrinogen IX]].<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 [[tetrapyrrole]] [[hydroxymethylbilane]] is converted by the action of [[uroporphyrinogen-III synthase]] to [[uroporphyrinogen III]].<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> Uroporphyrinogen III is subsequently converted into [[coproporphyrinogen III]], a conversion that entails four [[decarboxylation]]s:
+:uroporphyrinogen III   →   coproporphyrinogen III  +  4 CO<sub>2</sub>
+==Structural patterns of isomers==
+The difference between coproporphyrinogen I and III is the arrangements of the four [[propionic acid|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==
 <references />
 {{-}}
 [[File:Heme synthesis.png|center|framed|Heme synthesis—note that some reactions occur in the [[cytoplasm]] and some in the [[mitochondrion]] (yellow)]]