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I8250

Sigma-Aldrich

3-Iodo-L-tyrosine

Synonym(s):

3-Monoiodo-L-tyrosine

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About This Item

Linear Formula:
IC6H3-4-(OH)CH2CH(NH2)CO2H
CAS Number:
70-78-0
Molecular Weight:
307.09
Beilstein:
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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Jacqueline Studer et al.
Journal of forensic sciences, 59(6), 1650-1653 (2014-07-01)
Catecholamines, especially noradrenalin, are essential in the control of respiration and arousal. Thus, an impaired production of these neurotransmitters may contribute to the occurrence of sudden infant death syndrome (SIDS). The first step of the noradrenergic synthesis pathway is catalyzed
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
Mutations in the iodotyrosine deiodinase gene and hypothyroidism
Moreno J, et al.
The New England Journal of Medicine, 358(17), 1811-1818 (2008)
A new brain dopamine-deficient Drosophila and its pharmacological and genetic rescue
Cichewicz K, et al.
Genes, Brain, and Behavior, 16(3), 394-403 (2017)
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