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Merck

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:
Peso molecular:
314.17
Número MDL:
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
NACRES:
NA.77

product name

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

Nivel de calidad

solubilidad

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

temp. de almacenamiento

−20°C

cadena SMILES

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

Clave InChI

RKSUYBCOVNCALL-NTVURLEBSA-N

Información sobre el gen

human ... PAH(5053)

Descripción general

Tetrahydrobiopterin is a natural cofactor for phenylalanine hydroxylase, tyrosine hydroxylase, tryptophan hydroxylase, nitric oxide synthase and alkylglycerol monooxygenase.

Aplicación

(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.

Acciones bioquímicas o fisiológicas

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.

Características y beneficios

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.

Nota de preparación

(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.

Pictogramas

Exclamation mark

Palabra de señalización

Warning

Frases de peligro

Clasificaciones de peligro

Acute Tox. 4 Oral

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°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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Visite la Librería de documentos

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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