A cone-calix[4]arene derivative, featuring a guanidinium group and a Cu-II ion ligated to a I,4,7-triazacyclononane (TACN) ligand at the 1,3-distal positions of the upper rim, effectively catalyzes the cleavage of 2-hydroxypropyl p-nitrophenyl phosphate (HPNP) and a number of diriboimdeoside 3',5'-monophosphates (NpN'). Kinetic and potentiometric measurements support the operation of a general-base/general-acid mechanism and demonstrate that the hydroxo form of the ligated Cu-II ion is the sole catalytically active species. Rate enhancements relative to the background hydrolysis reaction at 1 mM catalyst concentration are 6 x 10(5)-fold for HPNP and cluster around 10(7)-fold with the most favorable catalyst-NpN' combinations.

Ribonuclease activity of an artificial catalyst that combines a ligated Cu(II) ion and a guanidinium group at the upper rim of a cone -calix[4]arene platform / Salvio, Riccardo; Volpi, Stefano; Cacciapaglia, Roberta; Casnati, Alessandro; Mandolini, Luigi; Sansone, Francesco. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 80:11(2015), pp. 5887-5893. [10.1021/acs.joc.5b00965]

Ribonuclease activity of an artificial catalyst that combines a ligated Cu(II) ion and a guanidinium group at the upper rim of a cone -calix[4]arene platform

VOLPI, STEFANO;CASNATI, Alessandro;SANSONE, Francesco
2015-01-01

Abstract

A cone-calix[4]arene derivative, featuring a guanidinium group and a Cu-II ion ligated to a I,4,7-triazacyclononane (TACN) ligand at the 1,3-distal positions of the upper rim, effectively catalyzes the cleavage of 2-hydroxypropyl p-nitrophenyl phosphate (HPNP) and a number of diriboimdeoside 3',5'-monophosphates (NpN'). Kinetic and potentiometric measurements support the operation of a general-base/general-acid mechanism and demonstrate that the hydroxo form of the ligated Cu-II ion is the sole catalytically active species. Rate enhancements relative to the background hydrolysis reaction at 1 mM catalyst concentration are 6 x 10(5)-fold for HPNP and cluster around 10(7)-fold with the most favorable catalyst-NpN' combinations.
Ribonuclease activity of an artificial catalyst that combines a ligated Cu(II) ion and a guanidinium group at the upper rim of a cone -calix[4]arene platform / Salvio, Riccardo; Volpi, Stefano; Cacciapaglia, Roberta; Casnati, Alessandro; Mandolini, Luigi; Sansone, Francesco. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 80:11(2015), pp. 5887-5893. [10.1021/acs.joc.5b00965]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2795955
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