Diiodtyrosine

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Structural formula
Structural formula of diiodotyrosine
General
Non-proprietary name Diiodtyrosine
other names
  • 3,5-diiodo- L- tyrosine
  • ( S ) -2-Amino-3- (4-hydroxy-3,5-diiodophenyl) propanoic acid
  • ( S ) -3,5-diiodo- L- tyrosine
Molecular formula C 9 H 9 I 2 NO 3
Brief description

beige solid

External identifiers / databases
CAS number 300-39-0
EC number 206-092-0
ECHA InfoCard 100.005.539
PubChem 6181
ChemSpider 8946
DrugBank DB03374
Wikidata Q410521
Drug information
ATC code

H03 BX01

Drug class

Other anti-thyroid drugs

properties
Molar mass 432.98 g mol −1
Physical state

firmly

Melting point

200 ° C

solubility

poor in water (617 mg l −1 at 20 ° C)

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 302 + 352-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Diiodtyrosine ( DIT ), also obsolete diiodotyrosine (DJT), is a non- proteinogenic amino acid that is formed from the proteinogenic amino acid L - tyrosine through iodination . In the human body it is the precursor of the thyroid hormones triiodothyronine (T 3 ) and thyroxine (T 4 ).

Diiodtyrosine is chiral . The natural substance is L- diiodotyrosine [synonym: ( S ) -diiodtyrosine]. If “Diiodtyrosine” is mentioned in the following text and in the scientific literature without any additional name ( prefix ), L- Diiodtyrosine is always meant.

Biological importance

→ Main article: Thyroid hormones - formation and release

Biosynthesis (human)

Diiodtyrosine is formed in the thyroid from L - tyrosine and iodide . The L- tyrosine is in the form of tyrosyl residues bound to thyroglobulin and the iodide is bound to the tyrosyl residues with the aid of the enzyme thyroid peroxidase (TPO); When one iodine atom binds, monoiodo tyrosine (MIT) is formed first , then diiodo tyrosine when another iodine atom binds. Since the TPO contains heme as a prosthetic group , the synthesis of MIT and DIT (and consequently that of the thyroid hormones) can be restricted by an iron deficiency .

Hormone precursor (human)

In humans, diiodtyrosine is the precursor substance of the thyroid hormone L - thyroxine (T 4 ) and one of the precursor substances of the thyroid hormone triiodothyronine (T 3 ).

use

Diiodtyrosine is used as a medicine for thyroid diseases ( thyreostatic ).

See also

Web links

Wikibooks: Biochemistry and Pathobiochemistry: Tyrosine Metabolism  - Learning and Teaching Materials

Individual evidence

  1. ↑ a b c d data sheet 3,5-Diiodo-L-tyrosine, 95% from AlfaAesar, accessed on December 25, 2019 ( PDF )(JavaScript required) .
  2. ↑ Entry on diiodtyrosine in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  3. ^ Section Physiology in "Thyroid" ( Memento from September 29, 2007 in the Internet Archive ) at DPC-Bühlmann GmbH.
  4. ↑ Article "Iodine" in the Lexicon for Orthomolecular Medicine - Vital Substance Lexicon
  5. ↑ Jörg Sasse: Plasma concentrations of prolactin, cortisol, thriiodothyronine and thyroxine in sleep deprivation responders with tryptophan depletion in the context of endogenous depression . Berlin 2000, DNB  959789901 , section 1.5.3 , urn : nbn: de: kobv: 11-10012126 (dissertation, Humboldt University Berlin).
  6. ↑ Katarzyna Agata Fischmann: Changes in the thyroid parameters TSH, fT3 and fT4 in the course of detoxification and withdrawal therapy in alcoholics . Tübingen 2005, DNB  97437086X , section 1.1.2 , urn : nbn: de: bsz: 21-opus-16593 (dissertation, Eberhard Karls University of Tübingen).
  7. ↑ ATC-H03BX01 entry (English) at ATC / DDD Index 2007