3,5-Diiodo-L-tyrosine dihydrate

Description

Diiodotyrosine does not possess pronounced hormonal activity. However, it stops production of thyrotropic hormone by the anterior lobe of the hypophysis, which activates thyroid gland activity.

Chemical properties

white to beige powder

The Uses of 3,5-Diiodo-L-tyrosine dihydrate

3,5-Diiodo-L-tyrosine Dihydrate is a thyroid hormone receptor agonist.

The Uses of 3,5-Diiodo-L-tyrosine dihydrate

It is used for hyperthyroid forms of endemic and sporadic goiters, diffuse, toxic goiters, and other illnesses accompanied by thyrotoxicity.

The Uses of 3,5-Diiodo-L-tyrosine dihydrate

3,5-Diiodo-L-tyrosine is a reactant used in the synthesis of fluorescent unnatural amino acids bearing stilbene or vinylene backbones. Also used in the discovery of potent heterodimeric antagonists of inhibitor of Apoptosis proteins with prolonged anti-tumor activity.

Definition

ChEBI: A diiodotyrosine that is L-tyrosine carrying iodo-substituents at positions C-3 and C-5 of the benzyl group. It is an intermediate in the thyroid hormone synthesis.

Synthesis

Diiodotyrosine, 3,5-diiodotyrosine (25.2.1), is synthesized by directly iodinating tyrosine with iodine in the presence of sodium iodide in aqueous ethylamine, or in a mixture of acetic and hydrochloric acids with the addition of hydrogen peroxide.

Purification Methods

It forms crystals from H2O [solubility (g/L): 0.204 at 0o, 1.86 at 50o, 5.6 at 75o and 17.0 at 100o]. Also recrystallise it from 50% or 70% EtOH. When boiled in EtOH the crystals swell, and on further boiling a gelatinous precipitate is formed [Harrington Biochem J 22 1434 1928, Jurd J Am Chem Soc 77 5747 1955]. It also crystallises from cold dilute ammonia on adding acetic acid to pH 6. [Beilstein 14 IV 2370.]