Deuteration of Indole Compounds: Synthesis of Deuterated Auxins, Indole-3-acetic Acid-d5 and Indole-3-butyric Acid-d5

[Image: see text] In this study, we describe a practical and facile synthesis of deuterium-labeled indoles via acid-catalyzed hydrogen–deuterium exchange. 3-Substituted indoles were efficiently deuterated through treatment with 20 wt % D(2)SO(4) in CD(3)OD at 60–90 °C. A deuterium incorporation reac...

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Autores principales: Yamada, Takeshi, Arai, Kazuki, Kikuchi, Rie, Okamoto, Sentaro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8340417/
https://www.ncbi.nlm.nih.gov/pubmed/34368582
http://dx.doi.org/10.1021/acsomega.1c02940
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author Yamada, Takeshi
Arai, Kazuki
Kikuchi, Rie
Okamoto, Sentaro
author_facet Yamada, Takeshi
Arai, Kazuki
Kikuchi, Rie
Okamoto, Sentaro
author_sort Yamada, Takeshi
collection PubMed
description [Image: see text] In this study, we describe a practical and facile synthesis of deuterium-labeled indoles via acid-catalyzed hydrogen–deuterium exchange. 3-Substituted indoles were efficiently deuterated through treatment with 20 wt % D(2)SO(4) in CD(3)OD at 60–90 °C. A deuterium incorporation reaction of 3-unsubstituted indoles was accomplished through treatment with CD(3)CO(2)D at 150 °C. The in situ preparation of a 20 wt % D(2)SO(4)/CH(3)OD/D(2)O solution enabled a large-scale and low-cost synthesis of auxins, indole-3-acetic acid-d5 and indole-3-butyric acid-d5.
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spelling pubmed-83404172021-08-06 Deuteration of Indole Compounds: Synthesis of Deuterated Auxins, Indole-3-acetic Acid-d5 and Indole-3-butyric Acid-d5 Yamada, Takeshi Arai, Kazuki Kikuchi, Rie Okamoto, Sentaro ACS Omega [Image: see text] In this study, we describe a practical and facile synthesis of deuterium-labeled indoles via acid-catalyzed hydrogen–deuterium exchange. 3-Substituted indoles were efficiently deuterated through treatment with 20 wt % D(2)SO(4) in CD(3)OD at 60–90 °C. A deuterium incorporation reaction of 3-unsubstituted indoles was accomplished through treatment with CD(3)CO(2)D at 150 °C. The in situ preparation of a 20 wt % D(2)SO(4)/CH(3)OD/D(2)O solution enabled a large-scale and low-cost synthesis of auxins, indole-3-acetic acid-d5 and indole-3-butyric acid-d5. American Chemical Society 2021-07-19 /pmc/articles/PMC8340417/ /pubmed/34368582 http://dx.doi.org/10.1021/acsomega.1c02940 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Yamada, Takeshi
Arai, Kazuki
Kikuchi, Rie
Okamoto, Sentaro
Deuteration of Indole Compounds: Synthesis of Deuterated Auxins, Indole-3-acetic Acid-d5 and Indole-3-butyric Acid-d5
title Deuteration of Indole Compounds: Synthesis of Deuterated Auxins, Indole-3-acetic Acid-d5 and Indole-3-butyric Acid-d5
title_full Deuteration of Indole Compounds: Synthesis of Deuterated Auxins, Indole-3-acetic Acid-d5 and Indole-3-butyric Acid-d5
title_fullStr Deuteration of Indole Compounds: Synthesis of Deuterated Auxins, Indole-3-acetic Acid-d5 and Indole-3-butyric Acid-d5
title_full_unstemmed Deuteration of Indole Compounds: Synthesis of Deuterated Auxins, Indole-3-acetic Acid-d5 and Indole-3-butyric Acid-d5
title_short Deuteration of Indole Compounds: Synthesis of Deuterated Auxins, Indole-3-acetic Acid-d5 and Indole-3-butyric Acid-d5
title_sort deuteration of indole compounds: synthesis of deuterated auxins, indole-3-acetic acid-d5 and indole-3-butyric acid-d5
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8340417/
https://www.ncbi.nlm.nih.gov/pubmed/34368582
http://dx.doi.org/10.1021/acsomega.1c02940
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