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Catalysis of a 1,3-dipolar reaction by distorted DNA incorporating a heterobimetallic platinum(ii) and copper(ii) complex
Department of Organic Chemistry I, Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad del País Vasco/Euskal Herriko Unibertsitatea (UPV/EHU), Donostia International Physics Center (DIPC), Donostia/San Sebastián, Spain.
Department of Organic Chemistry I, Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad del País Vasco/Euskal Herriko Unibertsitatea (UPV/EHU), Donostia International Physics Center (DIPC), Donostia/San Sebastián, Spain; Ikerbasque, Basque Foundation for Science, Bilbao, Spain.
Ikerbasque, Basque Foundation for Science, Bilbao, Spain; NanoBioSeparations Group, POLYMAT University of the Basque Country (UPV/EHU), Donostia/San Sebastián, Spain.
NanoBioSeparations Group, POLYMAT University of the Basque Country (UPV/EHU), Avda. Tolosa 72, E-20018 Donostia/San Sebastián, Spain.
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2017 (English)In: Chemical Science, ISSN 2041-6520, E-ISSN 2041-6539, Vol. 8, no 10, 7038-7046 p.Article in journal (Refereed) Published
Abstract [en]

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) [[small pi]4s + [small pi]2s] mechanisms leading to the exclusive formation of racemic endo-cycloadducts.

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2017. Vol. 8, no 10, 7038-7046 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:liu:diva-142960DOI: 10.1039/C7SC02311AISI: 000411730500038PubMedID: 29147531Scopus ID: 2-s2.0-85030084209OAI: oai:DiVA.org:liu-142960DiVA: diva2:1156481
Available from: 2017-11-13 Created: 2017-11-13 Last updated: 2017-12-07Bibliographically approved

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