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3-Iodotyrosine

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(Redirected fromMonoiodotyrosine)
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
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.000.677Edit this at Wikidata
MeSHMonoiodotyrosine
UNII
  • 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 ☒N
    Key: UQTZMGFTRHFAAM-ZETCQYMHSA-N ☒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
  • c1cc(c(cc1C[C@@H](C(=O)O)N)I)O
Properties
C9H10INO3
Molar mass307.087 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

3-Iodotyrosine is an intermediate in the synthesis ofthyroid hormones which is derived fromiodination oftyrosine at themeta-position of thebenzene ring. One unit can combine withdiiodotyrosine to formtriiodothyronine, as occurs in thecolloid of thethyroid follicle. Two units can combine to form3,3'-diiodothyronine.

3-Iodotyrosine is areversibleinhibitor of theenzymetyrosine hydroxylase.[2]

Relevance in dopamine studies

[edit]

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

References

[edit]
  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.doi:10.1016/S0021-9258(18)83654-7.PMID 2925666.
  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.S2CID 24808699.
  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.


Tyrosine / iodotyrosine
Thyronine / iodothyronine
Thyronamine / iodothyronamine
Iodothyroacetate / iodothyroacetic acid
Non-specific
AAADTooltip Aromatic L-amino acid decarboxylase
MAOTooltip Monoamine oxidase
Phenethylamines
(dopamine,epinephrine,
norepinephrine)
PAHTooltip Phenylalanine hydroxylase
THTooltip Tyrosine hydroxylase
DBHTooltip Dopamine beta-hydroxylase
PNMTTooltip Phenylethanolamine N-methyltransferase
COMTTooltip Catechol-O-methyl transferase
Tryptamines
(serotonin,melatonin)
TPHTooltip Tryptophan hydroxylase
AANATTooltip Serotonin N-acetyl transferase
ASMTTooltip Acetylserotonin O-methyltransferase
Histamine
HDCTooltip Histidine decarboxylase
HNMTTooltip Histamine N-methyltransferase
DAOTooltip Diamine oxidase
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