Formation of 3’,3’’,5’,5’’-tetrabromophenol sulfonphthalein from phenolsulfonphtalein catalyzed by chloroperoxidase of caldariomyces fumago

Chlorination of organic molecules is catalyzed by chloroperoxidase in the presence of hydrogen peroxide, few reports have been published on bromination of organic compounds catalyzed by chloroperoxidase. In this work, chloroperoxidase was used to catalyze the bromination of organic compounds in the presence of hydrogen peroxide and sodium bromide. The reaction mixture contain phenol red, NaBr, hydrogen peroxide and chloroperoxide, the reaction was followed by spectrophotometry and HPLC measurements at 590 nm. Chloroperoxidase catalyze the transformation of phenolsulfonphthalein (Phenol Red; PR) to 3’,3’’,5’,5’’- tetrabromophenolsulfonphthalein (Bromophenol Blue; BPB), under mild reaction conditions. The product of the reaction was characterized by HPLC-MS and FTIR. The reaction follows a Michaelis-Menten equation for NaBr, H2O2, and Phenol Red at different concentrations each. Maximum specific reaction rate has a values between 6.6 to 7.62 M-1 BPB formed min-1mg-1protein. Halogenation of phenol red with I, and Cl ions in the presence of chloroperoxidase was not detected. The main product of the reaction was Bromophenol blue, identified by HPLC-MS and FTIR analyses. Chloroperoxidase catalyze bromination reactions on organic compounds such as phenol red, thymol blue and cresol red. These capabilities might be used to produce a high value compounds.