T4425
(6R)-5,6,7,8-Tetrahydrobiopterin dihydrochloride
≥98% (HPLC), powder
Synonym(s):
(6R)-BH4
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About This Item
Empirical Formula (Hill Notation):
C9H15N5O3 · 2HCl
CAS Number:
Molecular Weight:
314.17
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
(6R)-5,6,7,8-Tetrahydrobiopterin dihydrochloride,
SMILES string
Cl.Cl.C[C@H](O)[C@H](O)[C@H]1CNC2=C(N1)C(=O)NC(N)=N2
InChI
1S/C9H15N5O3.2ClH/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7;;/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17);2*1H/t3-,4+,6-;;/m0../s1
InChI key
RKSUYBCOVNCALL-NTVURLEBSA-N
solubility
water, oxygen free: soluble 19.60-20.40 mg/mL, clear to slightly hazy, colorless to faintly yellow
storage temp.
−20°C
Quality Level
Gene Information
human ... PAH(5053)
Related Categories
General description
Tetrahydrobiopterin is a natural cofactor for phenylalanine hydroxylase, tyrosine hydroxylase, tryptophan hydroxylase, nitric oxide synthase and alkylglycerol monooxygenase.
Application
(6R)-BH4 has been used as a buffer component for assaying tyrosine hydroxylase enzyme activity in mouse brain tissues. (6R)-BH4 has also been identified as an activator compound from a LOPAC library screen using a fluorogenic α-glucosidase assay.
Biochem/physiol Actions
Lack of tetrahydrobiopterin may cause hyperphenylalaninemia. Diseases like, Parkinson′s, autism, depression and Alzheimer′s shows low concentration of tetrahydrobiopterin in the cerebrospinal fluid. This coenzyme participates in dopamine (DA) synthesis.
Features and Benefits
This compound is featured on the Dopamine, Norepinephrine and Epinephrine Synthesis and Nitric Oxide Synthases pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
Preparation Note
(6R)-5,6,7,8-Tetrahydrobiopterin dihydrochloride ((6R)-BH4 ) is soluble in oxygen free water at 19.60 - 20.40 mg/ml and yields a clear to slightly hazy, colorless to faint yellow solution.
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Katja Schmitz et al.
Neurotherapeutics : the journal of the American Society for Experimental NeuroTherapeutics, 18(3), 1862-1879 (2021-04-13)
Depletion of the enzyme cofactor, tetrahydrobiopterin (BH4), in T-cells was shown to prevent their proliferation upon receptor stimulation in models of allergic inflammation in mice, suggesting that BH4 drives autoimmunity. Hence, the clinically available BH4 drug (sapropterin) might increase the
José Carlos Rivera et al.
Journal of neuroinflammation, 14(1), 181-181 (2017-09-07)
Tetrahydrobiopterin (BH4) is an essential cofactor in multiple metabolic processes and plays an essential role in maintaining the inflammatory and neurovascular homeostasis. In this study, we have investigated the deleterious effects of BH4 deficiency on retinal vasculature during development. hph-1
E R Werner et al.
Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.), 203(1), 1-12 (1993-05-01)
Biosynthesis of tetrahydrobiopterin starts from guanosine triphosphate by the action of guanosine triphosphate cyclohydrolase I, which yields the first intermediate, 7,8-dihydroneopterin triphosphate. This compound is then converted by subsequent enzymes, 6-pyruvoyl tetrahydropterin synthase and sepiapterin reductase, to tetrahydrobiopterin, the biologically
Keun-Sung Lee et al.
The Korean journal of physiology & pharmacology : official journal of the Korean Physiological Society and the Korean Society of Pharmacology, 17(1), 89-97 (2013-02-27)
Developing an animal model for a specific disease is very important in the understanding of the underlying mechanism of the disease and allows testing of newly developed new drugs before human application. However, which of the plethora of experimental animal
Kwon, N.S., et al.
The Journal of Biological Chemistry, 264, 20498-20498 (1989)
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