Hydroxymethylbilane

Hydroxymethylbilane
Names
IUPAC name
3,3′,3′′,3′′′-[3,8,13,18-Tetrakis(carboxymethyl)-19-(hydroxymethyl)-5,10,15,22,23,24-hexahydro-21H-biline-2,7,12,17-tetrayl]tetrapropanoic acid
Systematic IUPAC name
3,3′,3′′,3′′′-[14,33,53,73-Tetrakis(carboxymethyl)-15-(hydroxymethyl)-11H,31H,51H,71H-1,7(2),3,5(2,5)-tetrapyrrolaheptaphane-13,34,54,74-tetrayl]tetrapropanoic acid
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference
 1209089
ChEBI
ChEMBL
ChemSpider
KEGG
MeSH hydroxymethylbilane
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C40H46N4O17/c45-17-32-25(12-40(60)61)21(4-8-36(52)53)29(44-32)15-31-24(11-39(58)59)20(3-7-35(50)51)28(43-31)14-30-23(10-38(56)57)19(2-6-34(48)49)27(42-30)13-26-22(9-37(54)55)18(16-41-26)1-5-33(46)47/h16,41-45H,1-15,17H2,(H,46,47)(H,48,49)(H,50,51)(H,52,53)(H,54,55)(H,56,57)(H,58,59)(H,60,61) checkY
    Key: WDFJYRZCZIUBPR-UHFFFAOYSA-N checkY
SMILES
  • O=C(O)Cc1c(c[nH]c1Cc2c(c(c([nH]2)Cc3[nH]c(c(c3CCC(=O)O)CC(=O)O)Cc4c(c(c([nH]4)CO)CC(=O)O)CCC(=O)O)CC(=O)O)CCC(=O)O)CCC(=O)O
Properties
Chemical formula
 C40H46N4O17
Molar mass 854.81 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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 a 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 in the overall reaction:[2][3]

4
 
2D representation of the chemical structure of porphobilinogen .
porphobilinogen
 
H2O
4 NH3
Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right
 
 
 
2D representation of the chemical structure of hydroxymethylbilane.
hydroxymethylbilane

The enzyme uroporphyrinogen III synthase catalyses the cyclisation reaction of hydroxymethylbilane into uroporphyrinogen III via a spiro intermediate which allows one of the pyrrole rings to convert its initial acetate to propionate configuration into a propionate-acetate one.[2][4][5]

2D representation of the chemical structure of hydroxymethylbilane .
hydroxymethylbilane
 
 
H2O
Rightward reaction arrow with minor product(s) to top and bottom right
 
H2O
 
2D representation of the chemical structure of uroporphyrinogen III .
uroporphyrinogen III

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.[6][7]

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. ^ Enzyme 2.5.1.61 at KEGG Pathway Database.
  4. ^ Battersby, Alan R.; Fookes, Christopher J. R.; Matcham, George W.J.; McDonald, Edward (1980). "Biosynthesis of the pigments of life: formation of the macrocycle". Nature. 285 (5759): 17–21. Bibcode:1980Natur.285...17B. doi:10.1038/285017a0. PMID 6769048. S2CID 9070849.
  5. ^ Enzyme 4.2.1.75 at KEGG Pathway Database.
  6. ^ 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.
  7. ^ 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.
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