C–H radiocyanation of bioactive molecules via sequential iodination/copper-mediated cross-coupling

This report describes a net C–H radiocyanation reaction for the transformation of electron rich (hetero)aromatic substrates into (11)CN-labeled products. Electrophilic C(sp(2))–H iodination of the (hetero)arene with N-iodosuccinimide is followed by Cu-mediated radiocyanation with K(11)CN. This seque...

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Detalles Bibliográficos
Autores principales: Horikawa, Mami, Joy, Stephen T., Sharninghausen, Liam S., Shao, Xia, Mapp, Anna K., Scott, Peter J. H., Sanford, Melanie S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10631240/
https://www.ncbi.nlm.nih.gov/pubmed/37969612
http://dx.doi.org/10.1039/d3sc03948j
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author Horikawa, Mami
Joy, Stephen T.
Sharninghausen, Liam S.
Shao, Xia
Mapp, Anna K.
Scott, Peter J. H.
Sanford, Melanie S.
author_facet Horikawa, Mami
Joy, Stephen T.
Sharninghausen, Liam S.
Shao, Xia
Mapp, Anna K.
Scott, Peter J. H.
Sanford, Melanie S.
author_sort Horikawa, Mami
collection PubMed
description This report describes a net C–H radiocyanation reaction for the transformation of electron rich (hetero)aromatic substrates into (11)CN-labeled products. Electrophilic C(sp(2))–H iodination of the (hetero)arene with N-iodosuccinimide is followed by Cu-mediated radiocyanation with K(11)CN. This sequence is applied to a variety of substrates, including the nucleobases uracil and cytosine, the amino acids tyrosine and tryptophan, and the peptide LYRAGWRAFS, which undergoes selective C–H radiocyanation at the tryptophan (W) residue.
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spelling pubmed-106312402023-11-15 C–H radiocyanation of bioactive molecules via sequential iodination/copper-mediated cross-coupling Horikawa, Mami Joy, Stephen T. Sharninghausen, Liam S. Shao, Xia Mapp, Anna K. Scott, Peter J. H. Sanford, Melanie S. Chem Sci Chemistry This report describes a net C–H radiocyanation reaction for the transformation of electron rich (hetero)aromatic substrates into (11)CN-labeled products. Electrophilic C(sp(2))–H iodination of the (hetero)arene with N-iodosuccinimide is followed by Cu-mediated radiocyanation with K(11)CN. This sequence is applied to a variety of substrates, including the nucleobases uracil and cytosine, the amino acids tyrosine and tryptophan, and the peptide LYRAGWRAFS, which undergoes selective C–H radiocyanation at the tryptophan (W) residue. The Royal Society of Chemistry 2023-10-20 /pmc/articles/PMC10631240/ /pubmed/37969612 http://dx.doi.org/10.1039/d3sc03948j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Horikawa, Mami
Joy, Stephen T.
Sharninghausen, Liam S.
Shao, Xia
Mapp, Anna K.
Scott, Peter J. H.
Sanford, Melanie S.
C–H radiocyanation of bioactive molecules via sequential iodination/copper-mediated cross-coupling
title C–H radiocyanation of bioactive molecules via sequential iodination/copper-mediated cross-coupling
title_full C–H radiocyanation of bioactive molecules via sequential iodination/copper-mediated cross-coupling
title_fullStr C–H radiocyanation of bioactive molecules via sequential iodination/copper-mediated cross-coupling
title_full_unstemmed C–H radiocyanation of bioactive molecules via sequential iodination/copper-mediated cross-coupling
title_short C–H radiocyanation of bioactive molecules via sequential iodination/copper-mediated cross-coupling
title_sort c–h radiocyanation of bioactive molecules via sequential iodination/copper-mediated cross-coupling
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10631240/
https://www.ncbi.nlm.nih.gov/pubmed/37969612
http://dx.doi.org/10.1039/d3sc03948j
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