Biopterin

Biopterin
Skeletal formula of biopterin
Ball-and-stick model of the biopterin molecule (tautomer CID 445040)
Names
IUPAC name
2-Amino-6-(1,2-dihydroxypropyl)-1H-pteridin-4-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.040.719 Edit this at Wikidata
KEGG
MeSH Biopterin
UNII
  • InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h2-3,6,15-16H,1H3,(H3,10,11,13,14,17)/t3-,6-/m0/s1 checkY
    Key: LHQIJBMDNUYRAM-DZSWIPIPSA-N checkY
  • InChI=1/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h2-3,6,15-16H,1H3,(H3,10,11,13,14,17)
    Key: LHQIJBMDNUYRAM-UHFFFAOYAC
  • InChI=1/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h2-3,6,15-16H,1H3,(H3,10,11,13,14,17)/t3-,6-/m0/s1
    Key: LHQIJBMDNUYRAM-DZSWIPIPBD
  • O=C2\N=C(/Nc1ncc(nc12)C(O)C(O)C)N
  • O=C2\N=C(/Nc1ncc(nc12)[C@@H](O)[C@@H](O)C)N
Properties
C9H11N5O3
Molar mass 237.216 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Biopterins are pterin derivatives which function as endogenous enzyme cofactors in many species of animals and in some bacteria and fungi. The prototypical compound of the class is biopterin (6-(1,2-dihydroxypropyl)-pterin), as shown in the infobox. Biopterins act as cofactors for aromatic amino acid hydroxylases (AAAH), which are involved in synthesizing a number of neurotransmitters including dopamine, norepinephrine, epinepherine, and serotonin, along with several trace amines. Nitric oxide synthesis also uses biopterin derivatives as cofactors. In humans, tetrahydrobiopterin (BH4) is the endogenous cofactor for AAAH enzymes.

As with pterins in general, biopterins exhibit tautomerism. In other words, there are a number of forms that readily interconvert, differing by the placement of hydrogen atoms. Depictions of the chemical structure may therefore vary among sources.[1]

  1. ^ Benkovic, Stephen J.; Sammons, Douglas; Armarego, Wilfred L. F.; Waring, Paul; Inners, Ruth (June 1985). "Tautomeric nature of quinonoid 6,7-dimethyl-7,8-dihydro-6H-pterin in aqueous solution: a nitrogen-15 NMR study". Journal of the American Chemical Society. 107 (12): 3706–3712. doi:10.1021/ja00298a048.