Abstract
MOLECULES which act as Lewis acids in the Michael reaction1 profoundly inhibit the activities of biological molecules, no doubt because they can alkylate sulphydryl groups and certain activated amines. Acrylonitrile rapidly and irreversibly alkylates proteins in mild conditions2 and recent findings strongly suggest3 that the cytotoxic compounds produced by irradiating carbohydrates may also act as acceptors in the Michael reactions. A variety of α,β-unsaturated carbonyl-containing compounds possess anti-bacterial, anti-cancer, and anti-viral activities3, -and in vivo conversion of the potent anti-tumour agent cyclophosphamide into acrolein4 suggests that acrolein may be the active cytotoxic agent. Furthermore, it is known that acrolein inhibits transcription in vitro by inhibiting RNA polymerase5.
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RANDO, R. In situ Generation of Irreversible Enzyme Inhibitors. Nature New Biology 237, 53 (1972). https://doi.org/10.1038/newbio237053a0
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DOI: https://doi.org/10.1038/newbio237053a0