Programmable Deuteration of Indoles via Reverse Deuterium Exchange

[Image: see text] Methods for selective deuterium incorporation into drug-like molecules have become extremely valuable due to the commercial, mechanistic, and biological importance of deuterated compounds. Herein, we report a programmable labeling platform that allows access to C2, C3, or C2- and C...

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Autores principales: Fitzgerald, Liam S., McNulty, Rachael L., Greener, Andrew, O’Duill, Miriam L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10407927/
https://www.ncbi.nlm.nih.gov/pubmed/37477980
http://dx.doi.org/10.1021/acs.joc.3c00819
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author Fitzgerald, Liam S.
McNulty, Rachael L.
Greener, Andrew
O’Duill, Miriam L.
author_facet Fitzgerald, Liam S.
McNulty, Rachael L.
Greener, Andrew
O’Duill, Miriam L.
author_sort Fitzgerald, Liam S.
collection PubMed
description [Image: see text] Methods for selective deuterium incorporation into drug-like molecules have become extremely valuable due to the commercial, mechanistic, and biological importance of deuterated compounds. Herein, we report a programmable labeling platform that allows access to C2, C3, or C2- and C3-deuterated indoles under mild, user-friendly conditions. The C2-deuterated indoles are accessed using a reverse hydrogen isotope exchange strategy which represents the first non-directed C2-deuteration of indoles.
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spelling pubmed-104079272023-08-09 Programmable Deuteration of Indoles via Reverse Deuterium Exchange Fitzgerald, Liam S. McNulty, Rachael L. Greener, Andrew O’Duill, Miriam L. J Org Chem [Image: see text] Methods for selective deuterium incorporation into drug-like molecules have become extremely valuable due to the commercial, mechanistic, and biological importance of deuterated compounds. Herein, we report a programmable labeling platform that allows access to C2, C3, or C2- and C3-deuterated indoles under mild, user-friendly conditions. The C2-deuterated indoles are accessed using a reverse hydrogen isotope exchange strategy which represents the first non-directed C2-deuteration of indoles. American Chemical Society 2023-07-21 /pmc/articles/PMC10407927/ /pubmed/37477980 http://dx.doi.org/10.1021/acs.joc.3c00819 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Fitzgerald, Liam S.
McNulty, Rachael L.
Greener, Andrew
O’Duill, Miriam L.
Programmable Deuteration of Indoles via Reverse Deuterium Exchange
title Programmable Deuteration of Indoles via Reverse Deuterium Exchange
title_full Programmable Deuteration of Indoles via Reverse Deuterium Exchange
title_fullStr Programmable Deuteration of Indoles via Reverse Deuterium Exchange
title_full_unstemmed Programmable Deuteration of Indoles via Reverse Deuterium Exchange
title_short Programmable Deuteration of Indoles via Reverse Deuterium Exchange
title_sort programmable deuteration of indoles via reverse deuterium exchange
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10407927/
https://www.ncbi.nlm.nih.gov/pubmed/37477980
http://dx.doi.org/10.1021/acs.joc.3c00819
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