Catalytic hydrolysis of dinitrophenyl sulfate by poly(ethylenimine) derivatives.

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  • Kunitake Toyoki
    Department of Organic Synthesis, Faculty of Engineering, Kyushu University
  • Sakamoto Tetsuo
    Department of Organic Synthesis, Faculty of Engineering, Kyushu University

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  • Catalytic Hydrolysis of Dinitrophenyl Sulfate by Poly(ethylenimine) Derivativest

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The catalytic hydrolysis of nitrophenyl sulfates by poly(ethylenimine)(PEI) derivatives was investigated at 30 °C in aqueous buffers. PEI derivatives which were made partly hydrophobic by incorporation of higher alkyl groups include alkylated PEI’s, quaternized PEI’s, and PEI’s with imidazole and hydroxamate functions. Nitrophenyl sulfates could not be cleaved by these polymers. The catalytic hydrolysis of 2-hydroxy-5-nitrophenyl sulfate by an PEI with imidazolylmethyl and dodecyl substituents failed to proceed in spite of the contrary report by Kiefer et al. 2,4-Dinitrophenyl sulfate was cleaved fairly readily by PEI derivatives. Simple sulfate transfer was observed in the case of alkylated PEI, but the catalytic hydrolysis proceeded according to the Michaelis-Menten kinetics in the case of quaternized PEI’s. Partly quaternized PEI’s showed highest catalytic efficiencies reported to date for the hydrolysis of dinitrophenyl sulfate.

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