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词条 Coproporphyrinogen I
释义

  1. Biosynthesys

  2. References

{{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=C36H44N4O8
| MolarMass=660.757 g/mol
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
}}Coproporphyrinogen I is an isomer of coproporphyrinogen III, a metabolic intermediate in the normal biosynthesis of heme. The compound is not normally produced by the human body; its production and accumulation causes a type of porphyria. [1]

The difference between coproporphyrinogen I and III is the arrangements of the four 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 enzyme uroporphyrinogen-III cosynthaseis missing or inactive, the compound uroporphyrinogen I is produced instead of uroporphyrinogen III. The enzyme uroporphyrinogen III decarboxylase will also act on the I isomer, producing coproporphyrinogen I:[2][1]

The reaction entails the conversion of the four carboxymethyl (acetic acid) side chains to methyl groups, with release of four molecules of carbon dioxide.

Unlike the III isomer, coproporphyrinogen I (which is cytotoxic) is not further processed by the body, and accumulates. This situation occurs in the pathological condition called congenital erythropoietic porphyria.[1]

References

1. ^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}}
2. ^{{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}}
{{Tetrapyrroles}}{{biochem-stub}}

1 : Tetrapyrroles

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