Construction of Peptide Macrocycles via Palladium-Catalyzed Multiple S-Arylation: An Effective Strategy to Expand the Structural Diversity of Cross-Linkers

Xin Chu; Linhua Shen; Bo Li; Peng Yang; Chengzhuo Du; Xiaoye Wang; Gang He; Samir Messaoudi; Gong Chen

doi:10.1021/acs.orglett.1c03003

Construction of Peptide Macrocycles via Palladium-Catalyzed Multiple S-Arylation: An Effective Strategy to Expand the Structural Diversity of Cross-Linkers

Xin Chu, Linhua Shen, Bo Li, Peng Yang, Chengzhuo Du, Xiaoye Wang, Gang He, Samir Messaoudi, Gong Chen

Research output: Contribution to journal › Article › peer-review

Abstract

A simple and versatile method for macrocyclizing unprotected native peptides with a wide range of easily accessible diiodo and triiodoarene reagents via the palladium-catalyzed multiple S-arylation of cysteine residues is developed. Iodoarenes with different arene and heteroarene cores can be incorporated into peptide macrocycles of varied ring sizes and amino acid compositions with high efficiency and selectivity under mild conditions.

Original language	English
Pages (from-to)	8001-8006
Number of pages	6
Journal	Organic Letters
Volume	23
Issue number	20
DOIs	https://doi.org/10.1021/acs.orglett.1c03003
Publication status	Published - 15 Oct 2021
Externally published	Yes

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10.1021/acs.orglett.1c03003

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title = "Construction of Peptide Macrocycles via Palladium-Catalyzed Multiple S-Arylation: An Effective Strategy to Expand the Structural Diversity of Cross-Linkers",

abstract = "A simple and versatile method for macrocyclizing unprotected native peptides with a wide range of easily accessible diiodo and triiodoarene reagents via the palladium-catalyzed multiple S-arylation of cysteine residues is developed. Iodoarenes with different arene and heteroarene cores can be incorporated into peptide macrocycles of varied ring sizes and amino acid compositions with high efficiency and selectivity under mild conditions.",

author = "Xin Chu and Linhua Shen and Bo Li and Peng Yang and Chengzhuo Du and Xiaoye Wang and Gang He and Samir Messaoudi and Gong Chen",

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T2 - An Effective Strategy to Expand the Structural Diversity of Cross-Linkers

AU - Chu, Xin

AU - Shen, Linhua

AU - Li, Bo

AU - Yang, Peng

AU - Du, Chengzhuo

AU - Wang, Xiaoye

AU - He, Gang

AU - Messaoudi, Samir

AU - Chen, Gong

PY - 2021/10/15

Y1 - 2021/10/15

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AB - A simple and versatile method for macrocyclizing unprotected native peptides with a wide range of easily accessible diiodo and triiodoarene reagents via the palladium-catalyzed multiple S-arylation of cysteine residues is developed. Iodoarenes with different arene and heteroarene cores can be incorporated into peptide macrocycles of varied ring sizes and amino acid compositions with high efficiency and selectivity under mild conditions.

U2 - 10.1021/acs.orglett.1c03003

DO - 10.1021/acs.orglett.1c03003

M3 - Article

C2 - 34582221

AN - SCOPUS:85116834656

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JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

Construction of Peptide Macrocycles via Palladium-Catalyzed Multiple S-Arylation: An Effective Strategy to Expand the Structural Diversity of Cross-Linkers

Abstract

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