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  • Title: Activation mechanism of tris(2,3-dibromopropyl)phosphate to the potent mutagen, 2-bromoacrolein.
    Author: Nelson SD, Omichinski JG, Iyer L, Gordon WP, Soderlund EJ, Dybing E.
    Journal: Biochem Biophys Res Commun; 1984 May 31; 121(1):213-9. PubMed ID: 6375666.
    Abstract:
    The potent mutagen 2- bromoacrolein is formed from the carcinogenic flame retardant tris(2,3-dibromopropyl)phosphate (Tris-BP) on incubation with hepatic microsomes. Substitution of deuterium for hydrogen at the terminal carbon atoms (C-3) of Tris-BP significantly decreased both the mutagenic response and the formation rate of 2- bromoacrolein . Mass spectral analysis of the 2- bromoacrolein that was formed from the selectively deuterated analogs of Tris-BP revealed that the primary mechanism for the formation of 2- bromoacrolein involves an initial oxidative dehalogenation at C-3 followed by a beta-elimination reaction.
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