3-Iodotyrosine

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
3-Iodotyrosine
3-Iodo-L-tyrosine
Names
IUPAC name
3-Iodotyrosine
Systematic IUPAC name
2-Amino-3-(4-hydroxy-3-iodophenyl)propanoic acid
Other names
Monoiodotyrosine; MIT[1]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.677 Edit this at Wikidata
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
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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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

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