期刊
CHEMICAL SCIENCE
卷 8, 期 10, 页码 7038-7046出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7sc02311a
关键词
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资金
- Spanish MINECO [CTQ2013-45415-P, CTQ2016-80375-P MAT2013-46006-R, CTQ2016-81797-REDC, PCIN-2015-240]
- Basque Government [IT673-13, PI-2013 57]
- ERC [209842]
- ERC PoC [713641]
- European Research Council (ERC) [713641, 209842] Funding Source: European Research Council (ERC)
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) [pi 4s + pi 2s] mechanisms leading to the exclusive formation of racemic endo-cycloadducts.
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