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]

Quick facts Names, Identifiers ...
Porphobilinogen
Names
Preferred IUPAC name
3-[5-(Aminomethyl)-4-(carboxymethyl)-1H-pyrrol-3-yl]propanoic acid
Identifiers
3D model (JSmol)
ChemSpider
DrugBank
ECHA InfoCard 100.006.970 Edit this at Wikidata
EC Number
  • 207-666-3
MeSH Porphobilinogen
UNII
  • InChI=1S/C10H14N2O4/c11-4-8-7(3-10(15)16)6(5-12-8)1-2-9(13)14/h5,12H,1-4,11H2,(H,13,14)(H,15,16) checkY
    Key: QSHWIQZFGQKFMA-UHFFFAOYSA-N checkY
  • C1=C(C(=C(N1)CN)CC(=O)O)CCC(=O)O
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]

2
 
 
2 H2O
Rightward reaction arrow with minor product(s) to top right
 
 
 

Metabolism

Next in the pathway towards porphyrins, four molecules of porphobilinogen are combined into hydroxymethyl bilane by the enzyme porphobilinogen deaminase:[2][3][4]

4
 
 
H2O
4 NH3
Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right
 
 
 

Pathologies

Acute intermittent porphyria causes an increase in urinary porphobilinogen.[5]

References

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