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I8250

Sigma-Aldrich

3-Iodo-L-tyrosine

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Synonym(s):
3-Monoiodo-L-tyrosine
Linear Formula:
IC6H3-4-(OH)CH2CH(NH2)CO2H
CAS Number:
Molecular Weight:
307.09
Beilstein/REAXYS Number:
2941266
EC Number:
MDL number:
UNSPSC Code:
12352200
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.32

Quality Level

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.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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