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Key Documents

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I8250

Sigma-Aldrich

3-Iodo-L-tyrosine

Sinónimos:

3-Monoiodo-L-tyrosine

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About This Item

Fórmula lineal:
IC6H3-4-(OH)CH2CH(NH2)CO2H
Número de CAS:
70-78-0
Peso molecular:
307.09
Beilstein/REAXYS Number:
2941266
EC Number:
200-744-8
MDL number:
MFCD00002608
UNSPSC Code:
12352200
eCl@ss:
32160406
PubChem Substance ID:
24278154
NACRES:
NA.32

impurities

~5% tyrosine

mp

210 °C (dec.) (lit.)

solubility

dilute aqueous acid: soluble

storage temp.

−20°C

SMILES string

N[C@@H](Cc1ccc(O)c(I)c1)C(O)=O

InChI

1S/C9H10INO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)/t7-/m0/s1

InChI key

UQTZMGFTRHFAAM-ZETCQYMHSA-N

Gene Information

human ... TH(7054)

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General description

Iodotyrosine coupled with di-iodotyrosine results in the synthesis of 3,5,3′-tri-iodothyronine (T3) or 3,3′,5′-tri-iodothyronine (rT3).

Application

3-Iodo-L-tyrosine has been used as an inhibitor for tyrosine hydroxylase enzyme in Drosophila and silkworm pupae.

Biochem/physiol Actions

3-iodotyrosine (3-IY) inhibits tyrosine hydroxylase that catalyzes levodopa (L-DOPA) formation from tyrosine. Iodotyrosine deiodinase enzyme deficiency leads to elevated levels of 3-IY in serum and urine in severe hypothyroidism and goiter.
TH (tyrosine 3-hydroxylase) is responsible for catalyzing the first step of the noradrenergic biosynthesis pathway. Mutations in TH are associated with tyrosine hydroxylase deficiency, leading to conditions such as infantile parkinsonism and DOPA (dopamine)-responsive dystonia as well as encephalopathy with perinatal onset.
Tyrosine hydroxylase inhibitor.

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)

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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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L G Harsing et al.
Neuroscience, 77(2), 419-429 (1997-03-01)
Striatal slices from the rat were preincubated with [3H]GABA and superfused in the presence of nipecotic acid and aminooxyacetic acid, inhibitors of high-affinity GABA transport and GABA aminotransferase, respectively. GABA efflux was estimated by monitoring tritium efflux, 98% of which
D K Ness et al.
Fundamental and applied toxicology : official journal of the Society of Toxicology, 30(2), 153-161 (1996-04-01)
Planarians (Dugesia dorotocephala) were evaluated as bioassay organisms to detect inhibition of tyrosine hydroxylase, the rate-limiting enzyme in the synthesis of catecholamines. Thirty planaria per dose were exposed to 0 (control), 0.001, 0.01, 0.1, or 1 mM 3-iodo-L-tyrosine (monoiodotyrosine or
Differential regulation of tyrosine hydroxylase in cuticular melanization and innate immunity in the silkworm Bombyx mori
Lee KS, et al.
Journal of Asia-Pacific Entomology, 18(4), 765-770 (2015)
P F Fitzpatrick
Biochemistry, 30(15), 3658-3662 (1991-04-16)
The steady-state kinetic mechanism for rat tyrosine hydroxylase has been determined by using recombinant enzyme expressed in insect tissue culture cells. Variation of any two of the three substrates, tyrosine, 6-methyltetrahydropterin, and oxygen, together at nonsaturating concentrations of the third
Dopamine and serotonin are both required for mate-copying in Drosophila melanogaster
Monier M, et al.
Frontiers in Behavioral Neuroscience, 12(3), 334-334 (2018)
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