Rhodium(III)-Catalyzed C–H Alkenylation: Access to Maleimide-Decorated Tryptophan and Tryptophan-Containing Peptides

Rhodium(III)-Catalyzed C–H Alkenylation: Access to Maleimide-Decorated Tryptophan and Tryptophan-Containing Peptides

Maleimide is widely applied in many fields, especially in antibody–drug conjugations and peptide drugs. Herein, we develop a strategy for the C–H alkenylation of tryptophan and tryptophan-containing peptides, providing a synthetic route of decorating maleimide on peptides. The method has a high tole...

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Bibliographic Details
Published in:Organic letters Vol. 22; no. 4; pp. 1535 - 1541
Main Authors: Peng, Jingjing, Li, Chunpu, Khamrakulov, Mirzadavlat, Wang, Jiang, Liu, Hong
Format: Journal Article
Language:English
Published: United States American Chemical Society 21-02-2020
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Summary:Maleimide is widely applied in many fields, especially in antibody–drug conjugations and peptide drugs. Herein, we develop a strategy for the C–H alkenylation of tryptophan and tryptophan-containing peptides, providing a synthetic route of decorating maleimide on peptides. The method has a high tolerance of functional groups and protecting groups. Furthermore, this method was applied to prepare peptide conjugation with molecules such as drugs and fluorescence probes. Moreover, macrocyclic peptides were obtained via this reaction.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c00086