Cinchona alkaloid derivatives featuring a guanidinium group in diverse positions efficiently catalyze the cleavage of the RNA model compound 2-hydroxypropyl p-nitrophenyl phosphate (HPNP). Their high catalytic efficiency as phosphodiesterases and the potentiometric and kinetic investigations indicate the existence of a high degree of cooperation between the guanidinium group and the quinuclidine moiety with the operation of a general acid/general base mechanism. The performance of these compounds was investigated and compared in the kinetic resolution of HPNP. These data were also compared with the results of DFT calculations on the transition states of the transesterification reaction that, in part, predict and rationalize the experimental data. © The Royal Society of Chemistry 2016.

Kinetic resolution of phosphoric diester by Cinchona alkaloid derivatives provided with a guanidinium unit / Salvio, Riccardo; Moliterno, Mauro; Caramelli, Dario; Pisciottani, Luca; Antenucci, Achille; D'Amico, Melania; Bella, Marco. - In: CATALYSIS SCIENCE & TECHNOLOGY. - ISSN 2044-4753. - STAMPA. - 6:7(2016), pp. 2280-2288. [10.1039/C5CY01208B]

Kinetic resolution of phosphoric diester by Cinchona alkaloid derivatives provided with a guanidinium unit

SALVIO, RICCARDO;MOLITERNO, MAURO;PISCIOTTANI, LUCA;ANTENUCCI, ACHILLE;BELLA, Marco
2016

Abstract

Cinchona alkaloid derivatives featuring a guanidinium group in diverse positions efficiently catalyze the cleavage of the RNA model compound 2-hydroxypropyl p-nitrophenyl phosphate (HPNP). Their high catalytic efficiency as phosphodiesterases and the potentiometric and kinetic investigations indicate the existence of a high degree of cooperation between the guanidinium group and the quinuclidine moiety with the operation of a general acid/general base mechanism. The performance of these compounds was investigated and compared in the kinetic resolution of HPNP. These data were also compared with the results of DFT calculations on the transition states of the transesterification reaction that, in part, predict and rationalize the experimental data. © The Royal Society of Chemistry 2016.
2016
Cinchona; alkaloid derivatives; kinetic resolution
01 Pubblicazione su rivista::01a Articolo in rivista
Kinetic resolution of phosphoric diester by Cinchona alkaloid derivatives provided with a guanidinium unit / Salvio, Riccardo; Moliterno, Mauro; Caramelli, Dario; Pisciottani, Luca; Antenucci, Achille; D'Amico, Melania; Bella, Marco. - In: CATALYSIS SCIENCE & TECHNOLOGY. - ISSN 2044-4753. - STAMPA. - 6:7(2016), pp. 2280-2288. [10.1039/C5CY01208B]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/850033
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