Selective Labeling of Peptides with O-Carboranes Via Manganese(I)-Catalyzed C-H Activation
Chemistry (Weinheim an der Bergstrasse, Germany)(2022)
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.
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Key words
carboranes,C-H alkenylation,chemoselectivity,manganese catalysis,peptide-diversification
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