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Key Documents

T4425

Sigma-Aldrich

(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
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

product name

(6R)-5,6,7,8-Tetrahydrobiopterin dihydrochloride,

Quality Level

solubility

water, oxygen free: soluble 19.60-20.40 mg/mL, clear to slightly hazy, colorless to faintly yellow

storage temp.

−20°C

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

Gene Information

human ... PAH(5053)

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Pteridines
Colette DS, et al.
reference module in biomedical sciences (2018)
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
Translational Medicine Strategies in Drug Development for Mood Disorders
Handbook of Biologically Active Peptides (2019)
Kwon, N.S., et al.
The Journal of Biological Chemistry, 264, 20498-20498 (1989)

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