Monoiodotyrosine

Structural formula
General
Surname	Monoiodotyrosine
other names	3-iodo- L- tyrosine ( S ) -2-Amino-3- (4-hydroxy-3-iodophenyl) propanoic acid ( S ) -Monoiodotyrosine
Molecular formula	C 9 H 10 INO 3
Brief description	white solid
External identifiers / databases
CAS number 70-78-0 [3-iodo- L- tyrosine] 25799-58-0 [3-iodo- D -tyrosine] 3078-39-5 [unspecified stereochemistry] EC number 200-744-8 ECHA InfoCard 100,000,677 PubChem 439744 ChemSpider 388804 DrugBank DB01758 Wikidata Q410703
properties
Molar mass	307.09 g mol −1
Physical state	firmly
Melting point	205 ° C
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Monoiodotyrosine ( MIT ) outdated even monoiodotyrosine (MJT), is a non proteinogenic amino acid selected from the proteinogenic amino acid L - tyrosine by iodination occurs. In the human body it is the precursor of the thyroid hormones triiodothyronine (T ₃ ) and thyroxine (T ₄ ).

Stereochemistry

Monoiodotyrosine is chiral . The natural product is L- monoiodotyrosine [synonym: ( S ) -monoiodotyrosine]. If “monoiodotyrosine” is mentioned in the following text and in the scientific literature without any additional name ( prefix ), it always means L -monoiodtyrosine.

Biological importance

→ Main article : Thyroid hormones - formation and release

Biosynthesis (human)

Monoiodotyrosine is produced 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 is produced first, and when another iodine atom binds, diiodo tyrosine (DIT) is produced. 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, monoiodtyrosine is one of the precursors of the thyroid hormone triiodothyronine (T ₃ ) and, via diiodtyrosine, the indirect precursor of the thyroid hormone L - thyroxine (T ₄ ).

See also

• albumin

Web links

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

• Thyroperoxidase ( EC  1.11.1.8 )
• Thyroxine 5'-deiodinase ( EC  1.97.1.10 )
• Thyroxine 5-deiodinase ( EC  1.97.1.11 )
• Diiodotyrosine transaminase ( EC  2.6.1.24 )

Individual evidence

1. ↑ Data monoiodotyrosine from Acros, accessed on 22 February, 2010.
2. ^ Entry on monoiodotyrosine in the ChemIDplus database of the United States National Library of Medicine (NLM) .
3. ↑ Data sheet 3-Iodo-L-tyrosine from Sigma-Aldrich , accessed on November 7, 2016 ( PDF ).
4. ^ Section Physiology in "Thyroid" ( Memento from September 29, 2007 in the Internet Archive ) at DPC-Bühlmann GmbH.
5. ↑ Article "Iodine" in the Lexicon for Orthomolecular Medicine - Vital Substance Lexicon
6. ↑ 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).
7. ↑ 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).

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !