Oxalyl thioesters are cell metabolites endowed with remarkably powerful acyl transfer abilities. The present article describes the bioinspired design of stable and activatable oxalyl thioester surrogates and their application for the modification of peptides and proteins. Formation of a stable oxalamide crosslink proceeds at rates ~30 M-1 s-1, in the nanomolar concentration range, in purified media or in protein extracts of cell lysates.
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