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M4758

Sigma-Aldrich

(±)-6-Methyl-5,6,7,8-tetrahydropterine dihydrochloride

~95% (TLC)

Synonym(s):

6-MPH4, DL-2-Amino-4-hydroxy-6-methyl-5,6,7,8-tetrahydropteridine dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C7H11N5O · 2HCl
CAS Number:
69113-63-9
Molecular Weight:
254.12
Beilstein/REAXYS Number:
5648114
MDL number:
MFCD00058175
UNSPSC Code:
12352204
PubChem Substance ID:
24896941
NACRES:
NA.51

assay

~95% (TLC)

Quality Level

200

storage temp.

−20°C

SMILES string

Cl.Cl.CC1CNc2nc(N)nc(O)c2N1

InChI

1S/C7H11N5O.2ClH/c1-3-2-9-5-4(10-3)6(13)12-7(8)11-5;;/h3,10H,2H2,1H3,(H4,8,9,11,12,13);2*1H

InChI key

MKQLORLCFAZASZ-UHFFFAOYSA-N

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Application

6-MPH4 is used to study mechanisms of nitric oxide (NO) synthase and free radical induced L-DOPA release from striatal tissue.

Biochem/physiol Actions

Synthetic cofactor for tyrosine hydrolase; also cofactor for phenylalanine and tryptophan hydroxylases; less activity than the natural cofactor, BH4

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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L-Tryptophan reagent grade, ≥98% (HPLC)

Sigma-Aldrich

T0254

L-Tryptophan

Elizabeth A Gaskell et al.
PloS one, 4(3), e4801-e4801 (2009-03-12)
The genome of the protozoan parasite Toxoplasma gondii was found to contain two genes encoding tyrosine hydroxylase; that produces L-DOPA. The encoded enzymes metabolize phenylalanine as well as tyrosine with substrate preference for tyrosine. Thus the enzymes catabolize phenylalanine to
P Abreu-González et al.
European journal of pharmacology, 541(1-2), 33-37 (2006-06-06)
In the present study we have analyzed the effect of tetrahydrobiopterin (BH4) essential cofactor for tyrosine hydroxylase and nitric oxide synthase, on the 3,4-dihydroxyphenylalanine (L-DOPA) release from in vitro incubated striatal tissue. dl-6-methyl-5,6,7,8 tetrahydropterine (6-MPH4)-stimulated L-DOPA release in a concentration-dependent
M Bauer et al.
Journal of neurochemistry, 82(5), 1300-1310 (2002-10-03)
Glial cell line-derived neurotrophic factor (GDNF) protects dopaminergic neurones against toxic and physical damage. In addition, GDNF promotes differentiation and structural integrity of dopaminergic neurones. Here we show that GDNF can support the function of primary dopaminergic neurones by triggering
J R Bostwick et al.
Analytical biochemistry, 192(1), 125-130 (1991-01-01)
A radiometric assay for tyrosine hydroxylase employing a coupled nonenzymatic decarboxylation of L-[14C]Dopa formed from L-[14C]tyrosine has been adapted for performance in a 96 microwell culture plate. The method uses an easily manufactured plate holder to compress blotting paper impregnated
F García-Molina et al.
Biochimica et biophysica acta, 1794(12), 1766-1774 (2009-08-22)
There is controversy in the literature concerning the action of tetrahydropterines on the enzyme tyrosinase and on melanogenesis in general. In this study, we demonstrate that tetrahydropterines can inhibit melanogenesis in several ways: i) by non-enzymatic inhibition involving purely chemical
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