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Selective Labeling of Peptides with o ‐Carboranes via Manganese(I)‐Catalyzed C−H Activation
Author(s) -
Jei Becky Bongsuiru,
Yang Long,
Ackermann Lutz
Publication year - 2022
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202200811
Subject(s) - manganese , chemistry , catalysis , stereoselectivity , carborane , combinatorial chemistry , boron , tryptophan , peptide , stereochemistry , organic chemistry , amino acid , biochemistry
Abstract A robust method for the selective labeling of peptides via manganese(I) catalysis was devised to achieve the C‐2 alkenylation of tryptophan containing peptides with 1‐ethynyl‐ o ‐carboranes. The manganese‐catalyzed C−H activation was accomplished with high catalytic efficiency, and featured low toxicity, high functional group tolerance and excellent E‐ stereoselectivity. This approach unravels a promising tool for the assembly of o ‐carborane with structurally complex peptides of relevance to applications in boron neutron capture therapy.