Synthesis of a dinuclear ZnII-calix[4]arene enzyme model with additional general base groups-catalytic activity in phosphate diester transesterification

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Abstract

Calix[4]arenes modified at the upper rim with two pairs of functional groups were synthesized and were used as starting materials for the synthesis of an enzyme model 3-Zn2 that has two ZnII centers and two dimethylamino groups. Under neutral conditions, this dinuclear metallo-enzyme model is catalytically active in the cleavage of the phosphate diester bond of the RNA model substrate 2-hydroxypropyl-p-nitrophenyl phosphate (HPNP). The kinetics of 3-Zn2 were compared with a mononuclear complex 1-Zn and a dinuclear complex 2-Zn2 that lack the dimethylamino groups. A catalysis mechanism is proposed where the ZnII centers of 3-Zn2 cooperate in the activation of the phosphoryl group while one of the dimethylamino groups acts as a general base in the deprotonation of the hydroxyl group of HPNP.
Original languageUndefined
Pages (from-to)3269-3275
JournalEuropean journal of organic chemistry
Volume1999
Issue number12
DOIs
Publication statusPublished - 1999

Keywords

  • METIS-106260
  • Calixarenes
  • IR-11633
  • Phosphatases
  • Zinc
  • Transesterification
  • Enzyme mimetics

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