イギリスの王立化学会発行の学術雑誌 Chemical Science
2021年10月号 Front Coverに選ばれました。
21 October 2021, Issue 39
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.