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D0387

Sigma-Aldrich

6,7-Dimethyl-5,6,7,8-tetrahydropterine hydrochloride

≥95%

Synonym(s):

2-Amino-6,7-dimethyl-4-hydroxy-5,6,7,8-tetrahydropteridine, DMPH4

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About This Item

Empirical Formula (Hill Notation):
C8H13N5O · HCl
CAS Number:
945-43-7
Molecular Weight:
231.68
MDL number:
MFCD00012731
UNSPSC Code:
12352100
PubChem Substance ID:
57654058
NACRES:
NA.22

Quality Level

100

Assay

≥95%

form

powder

storage temp.

−20°C

SMILES string

Cl[H].CC1Nc2nc(N)nc(O)c2NC1C

InChI

1S/C8H13N5O.ClH/c1-3-4(2)11-6-5(10-3)7(14)13-8(9)12-6;/h3-4,10H,1-2H3,(H4,9,11,12,13,14);1H

InChI key

GIHYTRGUZVYCQX-UHFFFAOYSA-N

Related Categories

Biochem/physiol Actions

Synthetic reduced pterin cofactor for nitric oxide synthetase, and for phenylalanine, tyrosine, and tryptophan hydroxylases; less active than the natural cofactor, tetrahydrobiopterin (BH4).

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H315,H318,H335

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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H Nakata et al.
Journal of biochemistry, 90(2), 567-569 (1981-08-01)
A simple and rapid method for isolating tryptophan 5-monooxygenase [L-tryptophan, tetrahydropteridine:oxygen oxidoreductase (5-hydroxylating), EC 1.14.16.4] was reported. The method involves adsorption on calcium phosphate gel and affinity chromatography on agarose coupled with dimethyltetrahydropteridine. Tryptophan 5-monooxygenase was purified 1,100-fold from a
M A Parniak et al.
The Journal of biological chemistry, 263(3), 1223-1230 (1988-01-25)
The pH optimum of rat liver phenylalanine hydroxylase is dependent on the structure of the cofactor employed and on the state of activation of the enzyme. The tetrahydrobiopterin-dependent activity of native phenylalanine hydroxylase has a pH optimum of about 8.5.
I G Jennings et al.
Proceedings of the National Academy of Sciences of the United States of America, 88(13), 5734-5738 (1991-07-01)
A monoclonal anti-idiotype antibody, NS7, previously shown to mimic the binding of the pterin cofactor of phenylalanine hydroxylase (phenylalanine 4-monooxygenase, EC 1.14.16.1) has been used to localize the cofactor binding site within the phenylalanine hydroxylase catalytic domain to a 27-amino-acid
S Koizumi et al.
Biochimica et biophysica acta, 789(2), 111-118 (1984-09-11)
A new microbial inhibitor for rat-liver phenylalanine hydroxylase (L-phenylalanine, tetrahydropteridine: oxygen oxidoreductase (4-hydroxylating), EC 1.14.16.1) was isolated from a culture medium of Fomes tasmanicus, and its structure was determined as 3,4-dihydroxystyrene. This compound inhibited the enzyme by 50% at a
M I Masana
Acta physiologica et pharmacologica latinoamericana : organo de la Asociacion Latinoamericana de Ciencias Fisiologicas y de la Asociacion Latinoamericana de Farmacologia, 34(3), 235-243 (1984-01-01)
Cholinergic modulation on the regulation of tyrosine hydroxylase was studied in guinea pig atria depolarized with high potassium concentration. In these conditions there was an increment in tyrosine hydroxylase activity as well as in the release of radioactivity from atria
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