Tagging Peptides with a Redox Responsive Fluorescent Probe Enabled by Photoredox Difunctionalization of Phenylacetylenes with Sulfinates and Disulfides

Liu，Hong1; Li，Guolin1,2; Peng，Zhiyuan1; Zhang，Shishuo1; Zhou，Xin1,2; Liu，Qingchao2; Wang，Junfeng3; Liu，Yonghong3; Jia，Tiezheng1,4

2022

10.1021/jacsau.2c00577

Journal of the American Chemical Society   Impact Factor & Quartile

0002-7863

1520-5126

Herein, we describe a photoredox three-component atom-transfer radical addition (ATRA) reaction of aryl alkynes directly with dialkyl disulfides and alkylsulfinates, circumventing the utilization of chemically unstable and synthetically challenging S-alkyl alkylthiosulfonates as viable addition partners. A vast array of (E)-β-alkylsulfonylvinyl alkylsulfides was prepared with great regio- and stereoselectivity. Moreover, this powerful tactic could be employed to tag cysteine residues of complex polypeptides in solution or on resin merging with solid phase peptide synthesis (SPPS) techniques. A sulfonyl-derived redox responsive fluorescent probe could be conveniently introduced on the peptide, which displays green fluorescence in cells while showing blue fluorescence in medium. The photophysical investigations reveal that the red shift of the emission fluorescence is attested to reduction of carbonyl group to the corresponding hydroxyl moiety. Interestingly, the fluorescence change of tagged peptide could be reverted in cells by treatment of H2O2, arising from the reoxidation of hydroxyl group back to ketone by the elevated level of reactive oxygen species (ROS).

Aryl Alkynes Difunctionalization Peptide Modification Photoredox Redox Responsive Fluorescent Probe

ESCI

English

NI Journal Papers

First

[2021B1515120046] ; [2022A1515011770] ; [2020B121201002] ; [31901786] ; [22078263]

Chemistry

Chemistry, Multidisciplinary

WOS:000889687500001

AMER CHEMICAL SOC

2-s2.0-85142621345

Scopus

1.Research Center for Chemical Biology and Omics Analysis,Department of Chemistry,Guangdong Provincial Key Laboratory of Catalysis,Southern University of Science and Technology,Shenzhen,1088 Xueyuan Blvd., Guangdong,518055,China
2.Department of Pharmaceutical Engineering,College of Chemical Engineering,Northwest University,Xi'an,Taibai North Road 229, Shanxi,710069,China
3.CAS Key Laboratory of Tropical Marine Bio-resources and Ecology,Guangdong Key Laboratory of Marine Materia Medica,Innovation Academy of South China Sea Ecology and Environmental Engineering,South China Sea Institute of Oceanology,Chinese Academy of Sciences,Guangzhou,164 West Xinggang Road,510301,China
4.State Key Laboratory of Elemento-Organic Chemistry,Nankai University,Tianjin,94 Weijin Road,300071,China

Liu，Hong,Li，Guolin,Peng，Zhiyuan,et al. Tagging Peptides with a Redox Responsive Fluorescent Probe Enabled by Photoredox Difunctionalization of Phenylacetylenes with Sulfinates and Disulfides[J]. Journal of the American Chemical Society,2022.

Liu，Hong.,Li，Guolin.,Peng，Zhiyuan.,Zhang，Shishuo.,Zhou，Xin.,...&Jia，Tiezheng.(2022).Tagging Peptides with a Redox Responsive Fluorescent Probe Enabled by Photoredox Difunctionalization of Phenylacetylenes with Sulfinates and Disulfides.Journal of the American Chemical Society.

Liu，Hong,et al."Tagging Peptides with a Redox Responsive Fluorescent Probe Enabled by Photoredox Difunctionalization of Phenylacetylenes with Sulfinates and Disulfides".Journal of the American Chemical Society (2022).