Hydroxymethylbilane, also known as preuroporphyrinogen, is an organic compound that occurs in living organisms during the synthesis of porphyrins, a group of critical substances that include haemoglobin, myoglobin, and chlorophyll. The name is often abbreviated as HMB.

Structure

The compound is a substituted bilane, a chain of four pyrrole rings interconnected by methylene bridges −CH2−. The chain starts with a hydroxymethyl group −CH2−OH and ends with an hydrogen, in place of the respective methylene bridges. The other two carbon atoms of each pyrrole cycle are connected to an acetic acid group −CH2−COOH and a propionic acid group −CH2−CH2−COOH, in that order.[1]

Metabolism

HMB is generated from four molecules of porphobilinogen by the enzyme porphobilinogen deaminase:[2]

Biosynthesis of pre-uroporphyrinogen from porphobilinogen

The enzyme uroporphyrinogen III synthase closes the chain to form uroporphyrinogen III:[2]


Uroporphyrinogen III is a porphyrinogen, which is a class of compounds with the hexahydroporphine macrocycle. In the absence of the enzyme, the compound undergoes spontaneous cyclization and becomes uroporphyrinogen I.[3][4]

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. ^ a b Voet, Donald; Voet, Judith G. (2011). Biochemistry (4. ed.). Hoboken, NJ: Wiley. ISBN 978-0-470-57095-1.
  3. ^ 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.
  4. ^ Sassa, S.; Kappas, A. (2000). "Molecular aspects of the inherited porphyrias". Journal of Internal Medicine. 247 (2): 169–178. doi:10.1046/j.1365-2796.2000.00618.x. PMID 10692079. S2CID 36820694.