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Directed C(sp(3))–H arylation of tryptophan: transformation of the directing group into an activated amide

The 8-aminoquinoline (8AQ) directed C(sp(3))–H functionalization was applied in the synthesis of β-arylated tryptophan derivatives. The laborious protecting group reorganization towards α-amino acids compatible for solid phase peptide synthesis (SPPS) was cut short by the transformation of the direc...

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Autores principales: Nicke, Lennart, Horx, Philip, Harms, Klaus, Geyer, Armin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6844298/
https://www.ncbi.nlm.nih.gov/pubmed/31803437
http://dx.doi.org/10.1039/c9sc03440d
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author Nicke, Lennart
Horx, Philip
Harms, Klaus
Geyer, Armin
author_facet Nicke, Lennart
Horx, Philip
Harms, Klaus
Geyer, Armin
author_sort Nicke, Lennart
collection PubMed
description The 8-aminoquinoline (8AQ) directed C(sp(3))–H functionalization was applied in the synthesis of β-arylated tryptophan derivatives. The laborious protecting group reorganization towards α-amino acids compatible for solid phase peptide synthesis (SPPS) was cut short by the transformation of the directing group into an activated amide, which was either used directly in peptide coupling or in the gram scale synthesis of storable Fmoc-protected amino acids for SPPS. In this work, directed C–H activation and nonplanar amide chemistry complement each other for the synthesis of hybrids between phenylalanine and tryptophan with restricted side chain mobility.
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spelling pubmed-68442982019-12-04 Directed C(sp(3))–H arylation of tryptophan: transformation of the directing group into an activated amide Nicke, Lennart Horx, Philip Harms, Klaus Geyer, Armin Chem Sci Chemistry The 8-aminoquinoline (8AQ) directed C(sp(3))–H functionalization was applied in the synthesis of β-arylated tryptophan derivatives. The laborious protecting group reorganization towards α-amino acids compatible for solid phase peptide synthesis (SPPS) was cut short by the transformation of the directing group into an activated amide, which was either used directly in peptide coupling or in the gram scale synthesis of storable Fmoc-protected amino acids for SPPS. In this work, directed C–H activation and nonplanar amide chemistry complement each other for the synthesis of hybrids between phenylalanine and tryptophan with restricted side chain mobility. Royal Society of Chemistry 2019-08-08 /pmc/articles/PMC6844298/ /pubmed/31803437 http://dx.doi.org/10.1039/c9sc03440d Text en This journal is © The Royal Society of Chemistry 2019 https://creativecommons.org/licenses/by/3.0/This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Nicke, Lennart
Horx, Philip
Harms, Klaus
Geyer, Armin
Directed C(sp(3))–H arylation of tryptophan: transformation of the directing group into an activated amide
title Directed C(sp(3))–H arylation of tryptophan: transformation of the directing group into an activated amide
title_full Directed C(sp(3))–H arylation of tryptophan: transformation of the directing group into an activated amide
title_fullStr Directed C(sp(3))–H arylation of tryptophan: transformation of the directing group into an activated amide
title_full_unstemmed Directed C(sp(3))–H arylation of tryptophan: transformation of the directing group into an activated amide
title_short Directed C(sp(3))–H arylation of tryptophan: transformation of the directing group into an activated amide
title_sort directed c(sp(3))–h arylation of tryptophan: transformation of the directing group into an activated amide
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6844298/
https://www.ncbi.nlm.nih.gov/pubmed/31803437
http://dx.doi.org/10.1039/c9sc03440d
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