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Biphasic electrochemical peptide synthesis
Authors:Shingo Nagahara  Yohei Okada  Yoshikazu Kitano  Kazuhiro Chiba
Affiliation:Department of Applied Biological Science, Tokyo University of Agriculture and Technology, 3-5-8- Saiwai-cho, Fuchu Tokyo 183-8509 Japan,
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 Created by potrace 1.16, written by Peter Selinger 2001-2019 O) as a stoichiometric byproduct. In combination with a soluble tag-assisted liquid-phase peptide synthesis, the selective recovery of desired peptides and Ph3P Created by potrace 1.16, written by Peter Selinger 2001-2019 O was achieved. Given that methods to reduce Ph3P Created by potrace 1.16, written by Peter Selinger 2001-2019 O to Ph3P have been reported, Ph3P Created by potrace 1.16, written by Peter Selinger 2001-2019 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.

The large amount of waste derived from coupling reagents is a serious drawback of peptide synthesis from a green chemistry viewpoint.
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