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Biphasic electrochemical peptide synthesis.

ABSTRACT: 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[double bond, length as m-dash]O) as a stoichiometric byproduct. In combination with a soluble tag-assisted liquid-phase peptide synthesis, the selective recovery of desired peptides and Ph₃P[double bond, length as m-dash]O was achieved. Given that methods to reduce Ph₃P[double bond, length as m-dash]O to Ph₃P have been reported, Ph₃P[double bond, length as m-dash]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.

SUBMITTER: Nagahara S

PROVIDER: S-EPMC8513919 | biostudies-literature | 2021 Oct

REPOSITORIES: biostudies-literature

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Biphasic electrochemical peptide synthesis.

Nagahara Shingo S Okada Yohei Y Kitano Yoshikazu Y Chiba Kazuhiro K

Chemical science 20210902 39

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 (Ph<sub>3</sub>P) generates a phosphine radical cation, which serves as the coupling reagent to activate carboxylic acids, and produces triphenylphosphine oxide (Ph<sub>3</sub>P[double bond, length as m-dash]O) as a stoichiometric byp ...[more]

PMID: 34745521

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