From Wikipedia, the free encyclopedia
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
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
100.000.677
MeSH
Monoiodotyrosine
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
C 9 H 10 I N O 3
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).
Chemical compound
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]
^ 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 .
^ 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 .
^ 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
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
Iodothyroacetate / iodothyroacetic acid