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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Molenveld, Peter and Engbersen, Johan F.J. and Reinhoudt, David N. (1999) Synthesis of a dinuclear ZnII-calix[4]arene enzyme model with additional general base groups-catalytic activity in phosphate diester transesterification. European Journal of Organic Chemistry, 1999 (12). pp. 3269-3275. ISSN 1434-193X

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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.
Item Type:Article
Copyright:© 1999 WILEY-VCH Verlag
Faculty:
Science and Technology (TNW)
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Link to this item:http://purl.utwente.nl/publications/11633
Official URL:http://dx.doi.org/10.1002/(SICI)1099-0690(199912)1999:12<3269::AID-EJOC3269>3.0.CO;2-V
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Metis ID: 106260