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Synfacts 2023; 19(07): 0731
DOI: 10.1055/s-0042-1752703
Peptide Chemistry

C–H Functionalization for the Synthesis of Maleimide-Decorated Peptides and Macrocyclic Peptides

Rezensent(en):
Hisashi Yamamoto
,
Isai Ramakrishna
Zhang Y, Hu S, Li Y, Wang Y, Yu T, Chen Q, Wang J, *, Liu H. * Shanghai Institute of Materia Medica, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Beijing, China Pharmaceutical University, Nanjing, and Nanjing University of Chinese Medicine, P. R. of China
Macrocyclization of Maleimide-Decorated Peptides via Late-Stage Rh(III)-Catalyzed Trp(C7) Alkenylation.

Org. Lett. 2023;
25: 2456-2460
DOI: 10.1021/acs.orglett.3c00601
CrossrefPubMedSuche in Google Scholar
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Key words

rhodium catalysis - C–H functionalization - macrocyclic peptides - tryptophan-containing peptides

Significance

Late-stage functionalization plays an inherent role in the construction of peptides and macrocyclic peptides. In the present study, the ­authors developed a Rh(III)-catalyzed alkenylation of tryptophan-containing peptides for the ­synthesis of maleimide-decorated peptides and macrocyclic peptides.


 

Comment

Rh(III)-catalyzed alkenylation of ­tryptophan-containing peptides proceeded smoothly to deliver maleimide-decorated peptides in good yields with excellent selectivity. The ­intramolecular reaction of maleimide-decorated peptides produced macrocyclic peptides.


 

 

Publikationsverlauf

Artikel online veröffentlicht:
16. Juni 2023

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