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T4425

Sigma-Aldrich

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

≥98% (HPLC), powder

Sinónimos:

(6R)-BH4

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About This Item

Fórmula empírica (notación de Hill):
C9H15N5O3 · 2HCl
Número de CAS:
69056-38-8
Peso molecular:
314.17
MDL number:
MFCD00891665
UNSPSC Code:
12352200
PubChem Substance ID:
24277922
NACRES:
NA.77

product name

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

Quality Level

200

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
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Kamil Kostyn et al.
Antioxidants (Basel, Switzerland), 9(8) (2020-08-14)
Catecholamines are biogenic aromatic amines common among both animals and plants. In animals, they are synthesized via tyrosine hydroxylation, while both hydroxylation or decarboxylation of tyrosine are possible in plants, depending on the species, though no tyrosine hydroxylase-a counterpart of
Tetrahydrobiopterin biosynthesis as a potential target of the kynurenine pathway metabolite xanthurenic acid
Haruki H, et al.
The Journal of Biological Chemistry (2016)
Ailing Fu et al.
Brain research, 1352, 208-213 (2010-07-06)
Glial-derived neurotrophic factor (GDNF) is a trophic factor for the nigra-striatal tract in experimental Parkinson's disease (PD). The neurotrophin must be administered by intra-cerebral injection, because GDNF does not cross the blood-brain barrier (BBB). In the present study, GDNF was
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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