Porphobilinogen
Intermediate in the biosynthesis of porphyrins
From Wikipedia, the free encyclopedia
Porphobilinogen (PBG) is an organic compound that occurs in living organisms as an intermediate in the biosynthesis of porphyrins, which include critical substances like hemoglobin and chlorophyll.[1]
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| Preferred IUPAC name
3-[5-(Aminomethyl)-4-(carboxymethyl)-1H-pyrrol-3-yl]propanoic acid | |
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3D model (JSmol) |
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| DrugBank | |
| ECHA InfoCard | 100.006.970 |
| EC Number |
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| MeSH | Porphobilinogen |
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CompTox Dashboard (EPA) |
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| Properties | |
| C10H14N2O4 | |
| Molar mass | 226.229 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The structure of the molecule can be described as molecule of pyrrole with sidechains substituted for hydrogen atoms at positions 2, 3 and 4 in the ring (1 being the nitrogen atom); respectively, an aminomethyl group −CH2−NH2, an acetic acid (carboxymethyl) group −CH2−COOH, and a propionic acid (carboxyethyl) group −CH2−CH2−COOH.
Biosynthesis
In an early step of the porphyrin biosynthesis pathway, porphobilinogen is generated from aminolevulinic acid (ALA) by the enzyme ALA dehydratase.[2]
Metabolism
Next in the pathway towards porphyrins, four molecules of porphobilinogen are combined into hydroxymethyl bilane by the enzyme porphobilinogen deaminase:[2][3][4]
Pathologies
Acute intermittent porphyria causes an increase in urinary porphobilinogen.[5]
