Catalysis of a 1, 3-dipolar reaction by distorted DNA incorporating a heterobimetallic platinum(ii) and copper(ii) complex. Issue 10 (30th August 2017)

• Record Type: Journal Article
• Authors: Rivilla, Iván; de Cózar, Abel; Schäfer, Thomas; Hernandez, Frank J.; Bittner, Alexander M.; Eleta-Lopez, Aitziber; Aboudzadeh, Ali; Santos, José I.; Miranda, José I.; Cossío, Fernando P.
• Is Part Of: Chemical science. Volume 8:Issue 10(2017)
• Page Start: 7038
• Page End: 7046
• Publication Date: 2017-08-30
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c7sc02311a
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A novel catalytic system based on covalently modified DNA is described. 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.