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- Name help_outline 3'-iodo-L-thyronine Identifier CHEBI:232695 Charge 0 Formula C15H14INO4 InChIKeyhelp_outline RUIUIJSMLKJUDC-ZDUSSCGKSA-N SMILEShelp_outline IC1=CC(OC2=CC=C(C[C@H]([NH3+])C([O-])=O)C=C2)=CC=C1O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline iodide Identifier CHEBI:16382 (Beilstein: 3587184; CAS: 20461-54-5) help_outline Charge -1 Formula I InChIKeyhelp_outline XMBWDFGMSWQBCA-UHFFFAOYSA-M SMILEShelp_outline [I-] 2D coordinates Mol file for the small molecule Search links Involved in 34 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline A Identifier CHEBI:13193 Charge Formula R SMILEShelp_outline * 2D coordinates Mol file for the small molecule Search links Involved in 3,001 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,932 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 3',5'-diiodo-L-thyronine Identifier CHEBI:195762 Charge 0 Formula C15H13I2NO4 InChIKeyhelp_outline LROTZSUGDZPWDN-ZDUSSCGKSA-N SMILEShelp_outline IC1=CC(OC2=CC=C(C[C@H]([NH3+])C([O-])=O)C=C2)=CC(I)=C1O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline AH2 Identifier CHEBI:17499 Charge 0 Formula RH2 SMILEShelp_outline *([H])[H] 2D coordinates Mol file for the small molecule Search links Involved in 2,929 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:82899 | RHEA:82900 | RHEA:82901 | RHEA:82902 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Study on the enzymatic 5'-deiodination of 3',5'-diiodothyronine using a radioimmunoassay for 3'-iodothyronine.
Visser T.J., van Overmeeren-Kaptein E.
A radioimmunoassay for 3'-iodothyronine has been developed. All iodothyronine analogues (except 3,3'-diiodothyronine) showed very litte (0.02% at most) cross-reactivity, and the assay was sensitive to 1 pg 3'-iodothyronine/tube. We have studied the 5'-deiodination of 3'-5'-diiodothyronine by rat l ... >> More
A radioimmunoassay for 3'-iodothyronine has been developed. All iodothyronine analogues (except 3,3'-diiodothyronine) showed very litte (0.02% at most) cross-reactivity, and the assay was sensitive to 1 pg 3'-iodothyronine/tube. We have studied the 5'-deiodination of 3'-5'-diiodothyronine by rat liver microsomal fraction in the presence of dithiothreitol. Production of 3'-iodothyronine at 37 degrees C was found to be linear with time of incubation up to 30 min and with concentration of microsomal protein up to 100 microgram/ml. The reaction rate reached a limit on increasing 3',5'-diiodothyronine concentration to 10 microM. The effect of pH on 3'-iodothyronine production was found to depend on 3',5'-diiodothyronine concentration. Increasing 3,5'-diiodothyronine concentration from 0.1 to 10 microM resulted in a shjift of the pH optimum from 6-6.5 to 7.5. Similar effects on the 5'-deiodination of 3,3',5'-triiodothyronine were observed, supporting the hypothesis that these reactions are catalysed by a single enzyme (iodothyronine 5'-deiodinase). << Less
Biochim Biophys Acta 631:246-252(1980) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.
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3',5'-diiodothyronine to 3'-monoiodothyronine conversion in the fed and fasted rat: enzyme characteristics and evidence for two distinct 5'-deiodinases.
Smallridge R.C., Burman K.D., Ward K.E., Wartofsky L., Dimond R.C., Wright F.D., Latham K.R.
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Development of a validated liquid chromatography/tandem mass spectrometry method for the distinction of thyronine and thyronamine constitutional isomers and for the identification of new deiodinase substrates.
Piehl S., Heberer T., Balizs G., Scanlan T.S., Koehrle J.
Thyronines (THs) and thyronamines (TAMs) are two groups of endogenous iodine-containing signaling molecules whose representatives differ from each other only regarding the number and/or the position of the iodine atoms. Both groups of compounds are substrates of three deiodinase isozymes, which ca ... >> More
Thyronines (THs) and thyronamines (TAMs) are two groups of endogenous iodine-containing signaling molecules whose representatives differ from each other only regarding the number and/or the position of the iodine atoms. Both groups of compounds are substrates of three deiodinase isozymes, which catalyze the sequential reductive removal of iodine from the respective precursor molecule. In this study, a novel analytical method applying liquid chromatography/tandem mass spectrometry (LC-MS/MS) was developed. This method permitted the unequivocal, simultaneous identification and quantification of all THs and TAMs in the same biological sample. Furthermore, a liquid-liquid extraction procedure permitting the concurrent isolation of all THs and TAMs from biological matrices, namely deiodinase (Dio) reaction mixtures, was established. Method validation experiments with extracted TH and TAM analytes demonstrated that the method was selective, devoid of matrix effects, sensitive, linear over a wide range of analyte concentrations and robust in terms of reproducible recoveries, process efficiencies as well as intra-assay and inter-assay stability parameters. The method was applied to study the deiodination reactions of iodinated THs catalyzed by the three deiodinase isozymes. With the HPLC protocol developed herein, sufficient chromatographic separation of all constitutional TH and TAM isomers was achieved. Accordingly, the position of each iodine atom removed from a TH substrate in a Dio-catalyzed reaction was backtracked unequivocally. While several established deiodination reactions were verified, two as yet unknown reactions, namely the phenolic ring deiodination of 3',5'-diiodothyronine (3',5'-T2) by Dio2 and the tyrosyl ring deiodination of 3-monoiodothyronine (3-T1) by Dio3, were newly identified. << Less
Rapid Commun. Mass Spectrom. 22:3286-3296(2008) [PubMed] [EuropePMC]
This publication is cited by 7 other entries.