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Synfacts 2023; 19(11): 1161
DOI: 10.1055/s-0042-1751615
Peptide Chemistry

Cu-Catalyzed Regioselective Chlorination of Peptides

Contributor(s):
Hisashi Yamamoto
,
Tomohiro Hattori
Nanjo T, *, Matsumoto A, Oshita T, Takemoto Y. * Kyoto University, Japan
Synthesis of Chlorinated Oligopeptides via γ- and δ-Selective Hydrogen Atom Transfer Enabled by the N-Chloropeptide Strategy.

J. Am. Chem. Soc. 2023;
145: 19067-19075
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Key words

chlorination - copper catalysis - peptides - hydrogen atom transfer

Significance

The late-stage diversification of structurally complex peptides bears enormous ­potential for drug discovery and construction of bioactive products. The authors have demon­strated a chlorination of peptides via selective ­hydrogen transfer of N-chloropeptides.


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Comment

The selective chlorination was performed for various dipeptides by the help of copper catalysis with high regioselectivity. Furthermore, the ­reaction could be applied for the introduction of three chlorine atoms by repetition of the standard reaction.


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Publication History

Article published online:
14 October 2023

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