Porphobilinogen

Intermediate in the biosynthesis of porphyrins
Porphobilinogen
Names
Preferred IUPAC name
3-[5-(Aminomethyl)-4-(carboxymethyl)-1H-pyrrol-3-yl]propanoic acid
Identifiers
CAS Number
  • 487-90-1 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 995 ☒N
DrugBank
  • DB02272 checkY
ECHA InfoCard 100.006.970 Edit this at Wikidata
EC Number
  • 207-666-3
MeSH Porphobilinogen
PubChem CID
  • 1021
UNII
  • 74KHC72QXK ☒N
CompTox Dashboard (EPA)
  • DTXSID4060070 Edit this at Wikidata
InChI
  • 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) ☒N
    Key: QSHWIQZFGQKFMA-UHFFFAOYSA-N ☒N
  • InChI=1/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)
    Key: QSHWIQZFGQKFMA-UHFFFAOYAF
  • C1=C(C(=C(N1)CN)CC(=O)O)CCC(=O)O
Properties
Chemical formula
 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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Infobox references
Chemical compound

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]

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 the first step of the porphyrin biosynthesis pathway, porphobilinogen is generated from aminolevulinate (ALA) by the enzyme ALA dehydratase.

File:Porphobilinogen-synthesis-from-ALA.png

Metabolism

In the typical porphyrin biosynthesis pathway, four molecules of porphobilinogen are concatenated by carbons 2 and 5 of the pyrrole ring (adjacent to the nitrogen atom) into hydroxymethyl bilane by the enzyme porphobilinogen deaminase, also known as hydroxymethylbilane synthase.

Pathologies

Acute intermittent porphyria causes an increase in urinary porphobilinogen.[2]

References

  1. ^ Paul R. Ortiz de Montellano (2008). "Hemes in Biology". Wiley Encyclopedia of Chemical Biology. John Wiley & Sons. doi:10.1002/9780470048672.wecb221. ISBN 978-0470048672.
  2. ^ Aarsand, AK; Petersen PH; Sandberg S (April 2006). "Estimation and application of biological variation of urinary delta-aminolevulinic acid and porphobilinogen in healthy individuals and in patients with acute intermittent porphyria". Clinical Chemistry. 52 (4): 650–656. doi:10.1373/clinchem.2005.060772. PMID 16595824.