Multifunctional hydrolytic catalysis. II. Hydrolysis of p-nitrophenyl acetate by a polymer catalyst which contains hydroxamate and imidazole functions

Toyoki Kunitake, Yoshio Okahata

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

A water-soluble polymer catalyst was prepared by radical polymerization of a protected hydroxamate monomer, 1-methyl-2-vinylimidazole and acrylamide, and by the subsequent NH2NH2 treatment of the polymer. The hydrolysis of p-nitrophenyl acetate by the bifunctional copolymer obeyed typical burst kinetics: rapid accumulation of acetyl hydroxamate group and its slow decomposition. The acetylation rate of the hydroxamate group was rather close to that of a polymer which does not contain the imidazole unit. However, the deacylation was markedly accelerated by the presence of the imidazole unit, and the difference in rate constants amounted to 60- to 80-fold at pH 8-9. These results indicate that the overall catalytic efficiency of the bifunctional polymer is enhanced due to the complementary action of the imidazole and hydroxamate functions.

Original languageEnglish
Pages (from-to)136-148
Number of pages13
JournalBioorganic Chemistry
Volume4
Issue number2
DOIs
Publication statusPublished - Jun 1975

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry

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