Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 31, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202206177
Keywords
C-H Activation; Macrocyclization; Peptide Modification; Rhodium; Tryptophan
Categories
Funding
- NSF of China [21922703, 91953112]
- National Key RAMP
- D Program of China [2019YFA0905800]
- Natural Science Foundation of Jiangsu Province [BK20190004, BK20202004]
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We report a method for late-stage peptide ligation and macrocyclization through rhodium-catalyzed alkylation of tryptophan residues at the C7 position. This study demonstrates site-selective peptide C-H alkylation through deconjugative isomerization using internal olefins. Our method provides access to peptide macrocycles with unique Trp(C7)-alkyl crosslinks and exhibits potent cytotoxicity towards cancer cells.
Transition metal-catalyzed C-H activation is a step-economical strategy for peptide functionalization. Herein, we report the method of late-stage peptide ligation and macrocyclization through rhodium-catalyzed alkylation of tryptophan residues at the C7 position. This method utilizes a N-(PBu2)-Bu-t directing group and tolerates various peptide and alkene substrates. Utilizing internal olefins, this study represents the first example of site-selective peptide C-H alkylation through deconjugative isomerization. Furthermore, our method provides access to peptide macrocycles with unique Trp(C7)-alkyl crosslinks and potent cytotoxicity towards cancer cells.
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