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Issue 10, 2017
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Catalysis of a 1,3-dipolar reaction by distorted DNA incorporating a heterobimetallic platinum(II) and copper(II) complex

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Abstract

A novel catalytic system based on covalently modified DNA is described. This catalyst promotes 1,3-dipolar reactions between azomethine ylides and maleimides. The catalytic system is based on the distortion of the double helix of DNA by means of the formation of Pt(II) adducts with guanine units. This distortion, similar to that generated in the interaction of DNA with platinum chemotherapeutic drugs, generates active sites that can accommodate N-metallated azomethine ylides. The proposed reaction mechanism, based on QM(DFT)/MM calculations, is compatible with thermally allowed concerted (but asynchronous) [π4s + π2s] mechanisms leading to the exclusive formation of racemic endo-cycloadducts.

Graphical abstract: Catalysis of a 1,3-dipolar reaction by distorted DNA incorporating a heterobimetallic platinum(ii) and copper(ii) complex

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Publication details

The article was received on 22 May 2017, accepted on 11 Aug 2017 and first published on 22 Aug 2017


Article type: Edge Article
DOI: 10.1039/C7SC02311A
Citation: Chem. Sci., 2017,8, 7038-7046
  • Open access: Creative Commons BY license
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    Catalysis of a 1,3-dipolar reaction by distorted DNA incorporating a heterobimetallic platinum(II) and copper(II) complex

    I. Rivilla, A. de Cózar, T. Schäfer, F. J. Hernandez, A. M. Bittner, A. Eleta-Lopez, A. Aboudzadeh, J. I. Santos, J. I. Miranda and F. P. Cossío, Chem. Sci., 2017, 8, 7038
    DOI: 10.1039/C7SC02311A

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