I8250
3-Iodo-L-tyrosine
Tyrosine hydroxylase inhibitor
Synonym(s):
3-Monoiodo-L-tyrosine
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About This Item
Linear Formula:
IC6H3-4-(OH)CH2CH(NH2)CO2H
CAS Number:
Molecular Weight:
307.09
NACRES:
NA.32
PubChem Substance ID:
eCl@ss:
32160406
UNSPSC Code:
12352200
EC Number:
200-744-8
MDL number:
Beilstein/REAXYS Number:
2941266
Product Name
3-Iodo-L-tyrosine,
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)
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
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Anionic iodotyrosine residues are required for iodothyronine synthesis
De Vijlder JJ and den Hartog MT
European Journal of Endocrinology, 138(2), 227-231 (1998)
Mutations in the iodotyrosine deiodinase gene and hypothyroidism
Moreno J, et al.
The New England Journal of Medicine, 358(17), 1811-1818 (2008)
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)