I8250

3-Iodo-L-tyrosine

• Synonym(s): 3-Monoiodo-L-tyrosine
• 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

Properties

• 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)

Description

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.

Safety Information

• 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