論文雑誌「Chemical Science」のカバーピクチャーを制作しました［東京農工大学］

Biphasic electrochemical peptide synthesis
Shingo Nagahara, Yohei Okada, Yoshikazu Kitano and Kazuhiro Chiba

The large amount of waste derived from coupling reagents is a serious drawback of peptide synthesis from a green chemistry viewpoint. To overcome this issue, we report an electrochemical peptide synthesis in a biphasic system. Anodic oxidation of triphenylphosphine (Ph₃P) generates a phosphine radical cation, which serves as the coupling reagent to activate carboxylic acids, and produces triphenylphosphine oxide (Ph₃P=O) as a stoichiometric byproduct. In combination with a soluble tag-assisted liquid-phase peptide synthesis, the selective recovery of desired peptides and Ph₃P=O was achieved. Given that methods to reduce Ph₃P=O to Ph₃P have been reported, Ph₃P=O could be a recyclable byproduct unlike byproducts from typical coupling reagents. Moreover, a commercial peptide active pharmaceutical ingredient (API), leuprorelin, was successfully synthesized without the use of traditional coupling reagents.

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