Halide-Mediated Electrochemical Peptide Synthesis Applicable to Highly Sterically Hindered Amino Acids

Electrochemical peptide synthesis using triaryl phosphines has been shown to be a promising approach for reducing the amount of waste in peptide synthesis. However, there is room for improvement from the viewpoint of the substrate scope. In this research, we succeeded in improving the reaction efficiency by utilizing a halide mediator. This method is applicable to highly sterically hindered amino acids, such as <i>N</i>-methyl phenylalanine. We also achieved the synthesis of icatibant, consisting of 10 amino acid residues.

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Publication Details

Journal
Organic Letters
Published
2026-02-05
DOI
https://doi.org/10.1021/acs.orglett.5c05139
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00
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article

Halide-Mediated Electrochemical Peptide Synthesis Applicable to Highly Sterically Hindered Amino Acids

Yoshikazu Kitano, Kazuhiro Chiba, Yohei Okada, Goki Hiratsuka et al.
Organic Letters
Radical Photochemical Reactions
article

Halide-Mediated Electrochemical Peptide Synthesis Applicable to Highly Sterically Hindered Amino Acids

Yoshikazu Kitano, Kazuhiro Chiba, Yohei Okada, Goki Hiratsuka, Shingo Shinjo-Nagahara
article en

Abstract

Electrochemical peptide synthesis using triaryl phosphines has been shown to be a promising approach for reducing the amount of waste in peptide synthesis. However, there is room for improvement from the viewpoint of the substrate scope. In this research, we succeeded in improving the reaction efficiency by utilizing a halide mediator. This method is applicable to highly sterically hindered amino acids, such as <i>N</i>-methyl phenylalanine. We also achieved the synthesis of icatibant, consisting of 10 amino acid residues.

Organic Letters
Tokyo University of Agriculture and Technology (JP)
Openalex Percentile: Top 65%
Radical Photochemical Reactions
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