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Streamlined construction of peptide macrocycles via palladium-catalyzed intramolecular S-arylation in solution and on DNA
A highly efficient and versatile method for construction of peptide macrocycles via palladium-catalyzed intramolecular S-arylation of alkyl and aryl thiols with aryl iodides under mild conditions is developed. The method exhibits a broad substrate scope for thiols, aryl iodides and amino acid units....
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179660/ https://www.ncbi.nlm.nih.gov/pubmed/34168804 http://dx.doi.org/10.1039/d1sc00789k |
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author | Yang, Peng Wang, Xuan Li, Bo Yang, Yixuan Yue, Jinfeng Suo, Yanrui Tong, Huarong He, Gang Lu, Xiaojie Chen, Gong |
author_facet | Yang, Peng Wang, Xuan Li, Bo Yang, Yixuan Yue, Jinfeng Suo, Yanrui Tong, Huarong He, Gang Lu, Xiaojie Chen, Gong |
author_sort | Yang, Peng |
collection | PubMed |
description | A highly efficient and versatile method for construction of peptide macrocycles via palladium-catalyzed intramolecular S-arylation of alkyl and aryl thiols with aryl iodides under mild conditions is developed. The method exhibits a broad substrate scope for thiols, aryl iodides and amino acid units. Peptide macrocycles of a wide range of size and composition can be readily assembled in high yield from various easily accessible building blocks. This method has been successfully employed to prepare an 8-million-membered tetrameric cyclic peptide DNA-encoded library (DEL). Preliminary screening of the DEL library against protein p300 identified compounds with single digit micromolar inhibition activity. |
format | Online Article Text |
id | pubmed-8179660 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-81796602021-06-23 Streamlined construction of peptide macrocycles via palladium-catalyzed intramolecular S-arylation in solution and on DNA Yang, Peng Wang, Xuan Li, Bo Yang, Yixuan Yue, Jinfeng Suo, Yanrui Tong, Huarong He, Gang Lu, Xiaojie Chen, Gong Chem Sci Chemistry A highly efficient and versatile method for construction of peptide macrocycles via palladium-catalyzed intramolecular S-arylation of alkyl and aryl thiols with aryl iodides under mild conditions is developed. The method exhibits a broad substrate scope for thiols, aryl iodides and amino acid units. Peptide macrocycles of a wide range of size and composition can be readily assembled in high yield from various easily accessible building blocks. This method has been successfully employed to prepare an 8-million-membered tetrameric cyclic peptide DNA-encoded library (DEL). Preliminary screening of the DEL library against protein p300 identified compounds with single digit micromolar inhibition activity. The Royal Society of Chemistry 2021-03-11 /pmc/articles/PMC8179660/ /pubmed/34168804 http://dx.doi.org/10.1039/d1sc00789k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Yang, Peng Wang, Xuan Li, Bo Yang, Yixuan Yue, Jinfeng Suo, Yanrui Tong, Huarong He, Gang Lu, Xiaojie Chen, Gong Streamlined construction of peptide macrocycles via palladium-catalyzed intramolecular S-arylation in solution and on DNA |
title | Streamlined construction of peptide macrocycles via palladium-catalyzed intramolecular S-arylation in solution and on DNA |
title_full | Streamlined construction of peptide macrocycles via palladium-catalyzed intramolecular S-arylation in solution and on DNA |
title_fullStr | Streamlined construction of peptide macrocycles via palladium-catalyzed intramolecular S-arylation in solution and on DNA |
title_full_unstemmed | Streamlined construction of peptide macrocycles via palladium-catalyzed intramolecular S-arylation in solution and on DNA |
title_short | Streamlined construction of peptide macrocycles via palladium-catalyzed intramolecular S-arylation in solution and on DNA |
title_sort | streamlined construction of peptide macrocycles via palladium-catalyzed intramolecular s-arylation in solution and on dna |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179660/ https://www.ncbi.nlm.nih.gov/pubmed/34168804 http://dx.doi.org/10.1039/d1sc00789k |
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