Peptide late-stage C(sp(3))–H arylation by native asparagine assistance without exogenous directing groups

There is a strong demand for novel native peptide motifs for post-synthetic modifications of peptides without pre-installation and subsequent removal of directing groups. Herein, we report an efficient method for peptide late-stage C(sp(3))–H arylations assisted by the unmodified side chain of aspar...

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Autores principales: Weng, Yiyi, Ding, Xingxing, Oliveira, João C. A., Xu, Xiaobin, Kaplaneris, Nikolaos, Zhu, Meijie, Chen, Hantao, Chen, Zhuo, Ackermann, Lutz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8161531/
https://www.ncbi.nlm.nih.gov/pubmed/34094199
http://dx.doi.org/10.1039/d0sc03830j
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author Weng, Yiyi
Ding, Xingxing
Oliveira, João C. A.
Xu, Xiaobin
Kaplaneris, Nikolaos
Zhu, Meijie
Chen, Hantao
Chen, Zhuo
Ackermann, Lutz
author_facet Weng, Yiyi
Ding, Xingxing
Oliveira, João C. A.
Xu, Xiaobin
Kaplaneris, Nikolaos
Zhu, Meijie
Chen, Hantao
Chen, Zhuo
Ackermann, Lutz
author_sort Weng, Yiyi
collection PubMed
description There is a strong demand for novel native peptide motifs for post-synthetic modifications of peptides without pre-installation and subsequent removal of directing groups. Herein, we report an efficient method for peptide late-stage C(sp(3))–H arylations assisted by the unmodified side chain of asparagine (Asn) without any exogenous directing group. Thereby, site-selective arylations of C(sp(3))–H bonds at the N-terminus of di-, tri-, and tetrapeptides have been achieved. Likewise, we have constructed a key building block for accessing agouti-related protein (AGRP) active loop analogues in a concise manner.
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spelling pubmed-81615312021-06-04 Peptide late-stage C(sp(3))–H arylation by native asparagine assistance without exogenous directing groups Weng, Yiyi Ding, Xingxing Oliveira, João C. A. Xu, Xiaobin Kaplaneris, Nikolaos Zhu, Meijie Chen, Hantao Chen, Zhuo Ackermann, Lutz Chem Sci Chemistry There is a strong demand for novel native peptide motifs for post-synthetic modifications of peptides without pre-installation and subsequent removal of directing groups. Herein, we report an efficient method for peptide late-stage C(sp(3))–H arylations assisted by the unmodified side chain of asparagine (Asn) without any exogenous directing group. Thereby, site-selective arylations of C(sp(3))–H bonds at the N-terminus of di-, tri-, and tetrapeptides have been achieved. Likewise, we have constructed a key building block for accessing agouti-related protein (AGRP) active loop analogues in a concise manner. The Royal Society of Chemistry 2020-08-12 /pmc/articles/PMC8161531/ /pubmed/34094199 http://dx.doi.org/10.1039/d0sc03830j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Weng, Yiyi
Ding, Xingxing
Oliveira, João C. A.
Xu, Xiaobin
Kaplaneris, Nikolaos
Zhu, Meijie
Chen, Hantao
Chen, Zhuo
Ackermann, Lutz
Peptide late-stage C(sp(3))–H arylation by native asparagine assistance without exogenous directing groups
title Peptide late-stage C(sp(3))–H arylation by native asparagine assistance without exogenous directing groups
title_full Peptide late-stage C(sp(3))–H arylation by native asparagine assistance without exogenous directing groups
title_fullStr Peptide late-stage C(sp(3))–H arylation by native asparagine assistance without exogenous directing groups
title_full_unstemmed Peptide late-stage C(sp(3))–H arylation by native asparagine assistance without exogenous directing groups
title_short Peptide late-stage C(sp(3))–H arylation by native asparagine assistance without exogenous directing groups
title_sort peptide late-stage c(sp(3))–h arylation by native asparagine assistance without exogenous directing groups
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8161531/
https://www.ncbi.nlm.nih.gov/pubmed/34094199
http://dx.doi.org/10.1039/d0sc03830j
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