Record Information
Version1.0
Creation date2015-10-09 22:30:26 UTC
Update date2017-01-19 02:36:22 UTC
FoodComEx IDPC000396
FoodDB RecordFDB022060
Chemical Information
NameBiopterin
DescriptionBiopterin concentrations in cerebrospinal fluid from patients with Parkinson's disease, in which the nigrostriatal dopamine neurons degenerate, are lower than those from age-matched older controls. In hereditary progressive dystonia/DOPA-responsive dystonia, which is a dopamine deficiency caused by mutations in GTP cyclohydrolase I without neuronal cell death (Segawa's disease), biopterin in cerebrospinal fluid decrease in parallel owing to the decreased activity in GTP cyclohydrolase I (EC 3.5.4.16, is an enzyme that is part of the folate and biopterin biosynthesis pathways. It is responsible for the hydrolysis of guanosine triphosphate (GTP) to form 7,8-dihydroneopterin 3'-triphosphate. (Pteridines (1999), 10(1), 5-13.) Lowered levels of urinary biopterin concomitant with elevated serum phenylalanine concentration occur in a variant type of hyperphenylalaninemia caused by a deficiency of tetrahydrobiopterin (BH4), the obligatory cofactor for phenylalanine hydroxylase. The most frequent form of this cofactor deficiency is due to lack of 6-pyruvoyl-tetrahydropterin synthase (PTPS) activity, the second enzyme in the biosynthetic pathway for BH4. (PMID 8178819) The hepatic phenylalanine hydroxylating system consists of 3 essential components, phenylalanine hydroxylase, dihydropteridine reductase, and the nonprotein coenzyme, tetrahydrobiopterin. The reductase and the pterin coenzyme are also essential components of the tyrosine and tryptophan hydroxylating systems. There are 3 distinct forms of phenylketonuria or hyperphenylalaninemia, each caused by lack of 1 of these essential components. The variant forms of the disease that are caused by the lack of dihydropteridine reductase or tetrahydrobiopterin are characterized by severe neurol. deterioration, impaired functioning of tyrosine and tryptophan hydroxylases, and the resultant deficiency of tyrosine- and tryptophan-derived monoamine neurotransmitters in brain. (PMID 3930837) [HMDB]
CAS Number22150-76-1
Structure
Thumb
Synonyms
SynonymSource
(-)-Biopterinhmdb
(1'R,1'S) Biopterinhmdb
[S-(R*,S*)]-2-amino-6-(1,2-dihydroxypropyl)-4(1H)-Pteridinonehmdb
2-amino-6-(L-erythro-1,2-dihydroxypropyl)-4(3H)-Pteridinonehmdb
6-Biopterinhmdb
Biopterinhmdb
L-Biopterinhmdb
L-erythro-Biopterinhmdb
Pterin H B2hmdb
Chemical FormulaC9H11N5O3
IUPAC name2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-4,8-dihydropteridin-4-one
InChI IdentifierInChI=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
InChI KeyLHQIJBMDNUYRAM-DZSWIPIPSA-N
Isomeric SMILESC[C@H](O)[C@H](O)C1=NC2=C(NC(N)=NC2=O)N=C1
Average Molecular Weight237.2153
Monoisotopic Molecular Weight237.086189243
Chemical Taxonomy
ClassificationNot classified
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 10 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci V0321
Cayman Chemical 10007662
Toronto Research Chemicals B389020