Journal
CHEMICAL SCIENCE
Volume 12, Issue 39, Pages 12911-12917Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1sc03023j
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Funding
- JSPS KAKENHI [17K19222, 19H00930, 19K22272, 16H06193, 17K19221, 21J11675]
- JST CREST [JPMJCR19R2]
- Grants-in-Aid for Scientific Research [21J11675, 19H00930, 19K22272] Funding Source: KAKEN
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An electrochemical peptide synthesis method has been developed to activate carboxylic acids in a biphasic system, with the stoichiometric byproduct Ph3P]O being recycled back into triphenylphosphine. This innovative approach not only reduces waste derived from coupling reagents, but also successfully synthesized a commercial peptide active pharmaceutical ingredient (API) leuprorelin without traditional coupling reagents.
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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