:3-Iodotyrosine

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| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 424914888

| ImageFile = (S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoic acid 200.svg

| ImageFile2 = 3-Iodotyrosine zwitterion 3D ball.png

| ImageCaption2 = 3-Iodo-L-tyrosine

| IUPACName = (2S)-2-Amino-3-(4-hydroxy-3-iodophenyl)propanoic acid

| OtherNames = Monoiodotyrosine; MIT{{cite journal |vauthors=Tietze F, Kohn LD, Kohn AD, etal |title=Carrier-mediated transport of monoiodotyrosine out of thyroid cell lysosomes |journal=J. Biol. Chem. |volume=264 |issue=9 |pages=4762–5 |date=March 1989 |doi=10.1016/S0021-9258(18)83654-7 |pmid=2925666 |doi-access=free }}

|Section1={{Chembox Identifiers

| CASNo = 3078-39-5

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = FRQ98U4U27

| CASNo_Comment = (DL)

| CASNo2 = 70-78-0

| CASNo2_Comment = (L)

| CASNo3 = 25799-58-0

| CASNo3_Comment = (D)

| MeSHName = Monoiodotyrosine

| IUPHAR_ligand = 5117

| PubChem = 6272

| PubChem_Comment = (DL)

| PubChem1 = 439744

| PubChem1_Comment = (L)

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 479789

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB01758

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 388804

| SMILES = c1cc(c(cc1C[C@@H](C(=O)O)N)I)O

| 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

| InChIKey = UQTZMGFTRHFAAM-ZETCQYMHBY

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = UQTZMGFTRHFAAM-ZETCQYMHSA-N

}}

|Section2={{Chembox Properties

| C=9 | H=10 | I=1 | N=1 | O=3

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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.{{cite journal | author = Richelson E | title = Properties of tyrosine hydroxylation in living mouse neuroblastoma clone N1E-115 | journal = Journal of Neurochemistry | volume = 27 | issue = 5 | pages = 1113–8 |date=November 1976 | pmid = 12170597 | doi = 10.1111/j.1471-4159.1976.tb00317.x| s2cid = 24808699 }}

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.{{Cite journal|last1=Fernandez|first1=Robert W.|last2=Akinleye|first2=Adesanya A.|last3=Nurilov|first3=Marat|last4=Feliciano|first4=Omar|last5=Lollar|first5=Matthew|last6=Aijuri|first6=Rami R.|last7=O'Donnell|first7=Janis M.|last8=Simon|first8=Anne F.|date=2017-08-01|title=Modulation of social space by dopamine in Drosophila melanogaster, but no effect on the avoidance of the Drosophila stress odorant|journal=Biology Letters|language=en|volume=13|issue=8|pages=20170369|doi=10.1098/rsbl.2017.0369|pmid=28794277|pmc=5582115|issn=1744-9561}}

References

{{Reflist}}

{{Thyroid hormone intermediates}}

{{Monoamine metabolism modulators}}

{{DEFAULTSORT:Iodotyrosine, 3-}}

Category:Iodinated tyrosine derivatives

Category:Tyrosine hydroxylase inhibitors