Photochemical Chemoselective Alkylation of TryptophanContaining Peptides

被引：51

作者：

Laroche, Benjamin ^{[1
]}

Tang, Xinjun ^{[1
]}

Archer, Gaetan ^{[1
]}

Di Sanza, Riccardo ^{[1
]}

Melchiorre, Paolo ^{[1
,2
]}

机构：

[1] ICIQ Inst Chem Res Catalonia, Barcelona Inst Sci & Technol, Tarragona 43007, Spain

[2] ICREA, Barcelona 08010, Spain

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 02期

基金：

欧洲研究理事会; 欧盟地平线“2020”;

关键词：

RADICAL TRIFLUOROMETHYLATION; CHARGE-TRANSFER; COMPLEX;

D O I：

10.1021/acs.orglett.0c03735

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a photochemical method for the chemoselective radical functionalization of tryptophan (Trp)-containing peptides. The method exploits the photoactivity of an electron donor-acceptor complex generated between the tryptophan unit and pyridinium salts. Irradiation with weak light (390 nm) generates radical intermediates right next to the targeted Trp amino acid, facilitating a proximity-driven radical functionalization. This protocol exhibits high chemoselectivity for Trp residues over other amino acids and tolerates biocompatible conditions.

引用

页码：285 / 289

页数：5

共 34 条

[1] Photocatalytic Modification of Amino Acids, Peptides, and Proteins [J].

Bottecchia, Cecilia ;

Noel, Timothy .

CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (01) :26-42

[2] Photoinduced deaminative strategies: Katritzky salts as alkyl radical precursors [J].

Correia, Jose Tiago M. ;

Fernandes, Vitor A. ;

Matsuo, Bianca T. ;

Delgado, Jose A. C. ;

de Souza, Wanderson C. ;

Paixao, Marcio Weber .

CHEMICAL COMMUNICATIONS, 2020, 56 (04) :503-514

[3] Synthetic Methods Driven by the Photoactivity of Electron Donor-Acceptor Complexes [J].

Crisenza, Giacomo E. M. ;

Mazzarella, Daniele ;

Melchiorre, Paolo .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (12) :5461-5476

[4] Chemistry glows green with photoredox catalysis [J].

Crisenza, Giacomo E. M. ;

Melchiorre, Paolo .

NATURE COMMUNICATIONS, 2020, 11 (01)

[5] Residue-Specific Peptide Modification: A Chemist's Guide [J].

deGruyter, Justine N. ;

Malins, Lara R. ;

Baran, Phil S. .

BIOCHEMISTRY, 2017, 56 (30) :3863-3873

[6] Selective Photoredox Trifluoromethylation of Tryptophan-Containing Peptides [J].

Ding, Bo ;

Weng, Yue ;

Liu, Yunqing ;

Song, Chunlan ;

Yin, Le ;

Yuan, Jiafan ;

Ren, Yanrui ;

Lei, Aiwen ;

Chiang, Chien-Wei .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (46) :7596-7605

[7] Positive photocatalysis of a diels-alder reaction by quenching of excited naphthalene-indole charge-transfer complex with cyclohexadiene [J].

Gonzalez-Bejar, Maria ;

Stiriba, Salah-Eddine ;

Miranda, Miguel A. ;

Perez-Prieto, Julia .

ORGANIC LETTERS, 2007, 9 (03) :453-456

[8] Cu-Catalyzed Site-Selective C(sp2)-H Radical Trifluoromethylation of Tryptophan-Containing Peptides [J].

Guerrero, Itziar ;

Correa, Arkaitz .

ORGANIC LETTERS, 2020, 22 (05) :1754-1759

[9] Chemo- and Regioselective Ethynylation of Tryptophan-Containing Peptides and Proteins [J].

Hansen, Morten Borre ;

Hubalek, Frantisek ;

Skrydstrup, Troels ;

Hoeg-Jensen, Thomas .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (05) :1572-1576

[10] Recent Advances in Pyridinium Salts as Radical Reservoirs in Organic Synthesis [J].

He, Fu-Sheng ;

Ye, Shengqing ;

Wu, Jie .

ACS CATALYSIS, 2019, 9 (10) :8943-8960

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