3-Iodotyrosine

3-Iodotyrosine
	; 3-Iodo-L-tyrosine
Names
	IUPAC name (2S)-2-Amino-3-(4-hydroxy-3-iodophenyl)propanoic acid
	Other names Monoiodotyrosine; MIT[1]
Identifiers
CAS Number	3078-39-5 (DL) ; 70-78-0 (L); 25799-58-0 (D);
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL479789 ;
ChemSpider	388804 ;
DrugBank	DB01758 ;
ECHA InfoCard	100.000.677
IUPHAR/BPS	5117;
MeSH	Monoiodotyrosine
PubChem CID	6272 (DL); 439744 (L);
CompTox Dashboard (EPA)	DTXSID1075353 ;
	InChI 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 Key: UQTZMGFTRHFAAM-ZETCQYMHSA-N ; InChI=1/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 Key: UQTZMGFTRHFAAM-ZETCQYMHBY;
	SMILES c1cc(c(cc1C[C@@H](C(=O)O)N)I)O;
Properties
Chemical formula	C9H10INO3
Molar mass	307.087 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

3-Iodotyrosine is an intermediate in the synthesis of thyroid hormones which is derived from iodination of tyrosine at the meta-position of the benzene ring. One unit can combine with diiodotyrosine to form triiodothyronine, as occurs in the colloid of the thyroid follicle. Two units can combine to form 3,3'-diiodothyronine.

3-Iodotyrosine is a reversible inhibitor of the enzyme tyrosine hydroxylase.[2]

Relevance in dopamine studies

3-Iodotyrosine, a pathway inhibitor in the synthesis of the neurotransmitter dopamine, was used to determine the effects of decreased dopamine levels in social spacing of Drosophila melanogaster. 3-4 day old flies that were fed 3-iodotyrosine for 24 hours were shown to have altered dopamine levels.[3]

References

Tietze F, Kohn LD, Kohn AD, et al. (March 1989). "Carrier-mediated transport of monoiodotyrosine out of thyroid cell lysosomes". J. Biol. Chem. 264 (9): 4762–5. PMID 2925666.
Richelson E (November 1976). "Properties of tyrosine hydroxylation in living mouse neuroblastoma clone N1E-115". Journal of Neurochemistry. 27 (5): 1113–8. doi:10.1111/j.1471-4159.1976.tb00317.x. PMID 12170597.
Fernandez, Robert W.; Akinleye, Adesanya A.; Nurilov, Marat; Feliciano, Omar; Lollar, Matthew; Aijuri, Rami R.; O'Donnell, Janis M.; Simon, Anne F. (2017-08-01). "Modulation of social space by dopamine in Drosophila melanogaster, but no effect on the avoidance of the Drosophila stress odorant". Biology Letters. 13 (8): 20170369. doi:10.1098/rsbl.2017.0369. ISSN 1744-9561. PMC 5582115. PMID 28794277.

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[pmid2925666-1] Tietze F, Kohn LD, Kohn AD, et al. (March 1989). "Carrier-mediated transport of monoiodotyrosine out of thyroid cell lysosomes". J. Biol. Chem. 264 (9): 4762–5. PMID 2925666.

[pmid12170597-2] Richelson E (November 1976). "Properties of tyrosine hydroxylation in living mouse neuroblastoma clone N1E-115". Journal of Neurochemistry. 27 (5): 1113–8. doi:10.1111/j.1471-4159.1976.tb00317.x. PMID 12170597.

[3] Fernandez, Robert W.; Akinleye, Adesanya A.; Nurilov, Marat; Feliciano, Omar; Lollar, Matthew; Aijuri, Rami R.; O'Donnell, Janis M.; Simon, Anne F. (2017-08-01). "Modulation of social space by dopamine in Drosophila melanogaster, but no effect on the avoidance of the Drosophila stress odorant". Biology Letters. 13 (8): 20170369. doi:10.1098/rsbl.2017.0369. ISSN 1744-9561. PMC 5582115. PMID 28794277.

Thyroid hormone metabolic intermediates
Tyrosine / iodotyrosine	3-Iodotyrosine Diiodotyrosine
Thyronine / iodothyronine	3'-Monoiodothyronine 3,3'-Diiodothyronine 3,5-Diiodothyronine 3,3',5-Triiodothyronine (T₃) 3,3',5'-Triiodothyronine (Reverse T₃) 3,5,3',5'-Tetraiodothyronine (Thyroxine, T₄)
Thyronamine / iodothyronamine	3-Iodothyronamine 3,3',5-Triiodothyronamine
Iodothyroacetate / iodothyroacetic acid	Triiodothyroacetate (TRIAC)