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Synfacts 2024; 20(04): 0429
DOI: 10.1055/s-0043-1773185
Peptide Chemistry

Recyclable Bicyclic Benziodazolone-Mediated Peptide Coupling Reaction

Contributor(s):
Hisashi Yamamoto
,
Kazumasa Kon
Uehara D, Adachi S, Tsubouchi A, Okada Y, Zhdankin VV, Yoshimura A, Saito A. * Tokyo University of Agriculture and Technology, Japan
Peptide Coupling Using Recyclable Bicyclic Benziodazolone.

Chem. Commun. 2024;
60: 956-959
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Key words

peptide coupling - bicyclic benziodazolones - recyclable reagent - triarylphosphines

Significance

The coupling reaction between carboxylic acids and amines using coupling reagents is generally used for the synthesis of peptides. However, this reaction generates a large amount of waste derived from the coupling reagent. The authors have developed a peptide coupling using recyclable bicyclic benziodazolones.


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Comment

This coupling reaction using bicyclic benziodazolones A or B produced various dipeptides in high to good yield. After the reaction, A and B could be recovered as I(I) species. Also, electrochemical oxidation of this I(I) species reproduced A and B, and these regenerated A and B promoted a peptide coupling reaction.


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Publication History

Article published online:
13 March 2024

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