Synfacts 2024; 20(01): 0101
DOI: 10.1055/s-0043-1772892
Peptide Chemistry

Late-Stage Modification of Oligopeptide Trp Units with Azoles

Contributor(s):
Hisashi Yamamoto
,
Tomohiro Hattori
Watanabe S, Wada Y, Kawano M, Higashibayashi S, Sugai T, Hanaya K. Keio University, Tokyo, Japan
Selective Modification of Tryptophan in Polypeptides via C–N Coupling with Azoles Using in situ Generated Iodine-Based Oxidants in Aqueous Media.

Chem. Commun. 2023;
59: 13026-13029
DOI: 10.1039/d3cc03731b.
 

Significance

The late-stage modification of ­oligopeptides is a straightforward strategy for the preparation of bioactive compounds. The authors have demonstrated a C–N coupling reaction in which azoles are incorporated into the Trp units of oligopeptides.


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Comment

The modification of Trp proceeded in aqueous media and various azole derivatives could be applied for this method by using a combination of KI, KIO3, and methanesulfonic acid.


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Publication History

Article published online:
08 December 2023

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