Diiodtyrosine
Structural formula | ||||||||||||||||||||||
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Non-proprietary name | Diiodtyrosine | |||||||||||||||||||||
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Molecular formula | C 9 H 9 I 2 NO 3 | |||||||||||||||||||||
Brief description |
beige solid |
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Molar mass | 432.98 g mol −1 | |||||||||||||||||||||
Physical state |
firmly |
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Melting point |
200 ° C |
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solubility |
poor in water (617 mg l −1 at 20 ° C) |
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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
- Thyroperoxidase (EC 1.11.1.8) (English) at ExPASy
- Thyroxine 5'-deiodinase (EC 1.97.1.10) (English) at ExPASy
- Thyroxine 5-deiodinase (EC 1.97.1.11) (English) at ExPASy
- Diiodotyrosine transaminase (EC 2.6.1.24) (English) at ExPASy
Individual evidence
- ↑ a b c d data sheet 3,5-Diiodo-L-tyrosine, 95% from AlfaAesar, accessed on December 25, 2019 ( PDF )(JavaScript required) .
- ↑ Entry on diiodtyrosine in the ChemIDplus database of the United States National Library of Medicine (NLM) .
- ^ Section Physiology in "Thyroid" ( Memento from September 29, 2007 in the Internet Archive ) at DPC-Bühlmann GmbH.
- ↑ Article "Iodine" in the Lexicon for Orthomolecular Medicine - Vital Substance Lexicon
- ↑ 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).
- ↑ 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).
- ↑ ATC-H03BX01 entry (English) at ATC / DDD Index 2007