Organic Chemistry of DNA Functionalization; Chromophores as DNA Base Substitutes versus DNA Base/2′-Modifications

Wolfgang Schmucker; Hans-Achim Wagenknecht

doi:10.1055/s-0032-1317158

Synlett, Table of Contents

Synlett 2012; 23(17): 2435-2448
DOI: 10.1055/s-0032-1317158

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Organic Chemistry of DNA Functionalization; Chromophores as DNA Base Substitutes versus DNA Base/2′-Modifications

Wolfgang Schmucker

Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany, Fax: +49(721)60844825 Email: wagenknecht@kit.edu

,

Hans-Achim Wagenknecht*

Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany, Fax: +49(721)60844825 Email: wagenknecht@kit.edu

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Abstract

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Abstract

Nucleic acids are suitable scaffolds for the precise arrangement of different kinds of artificial functionalities inside or along the double helix. In this account, we summarize our synthetic efforts over the last ten years to modify DNA chemically with organic chromophores, fluorescent probes, and metal-ion ligands. We used three different approaches: (i) replacement of DNA bases (substitutes/surrogates), (ii) modifications of DNA bases (mainly 2′-deoxyuridine), and (iii) sugar modifications at the 2′-position. The first two types of modifications were achieved mainly by the DNA building block approach, whereas the latter type is based on postsynthetic methodologies. The different synthetic concepts are described and the influence of representative modifications on the melting temperature is compared.

Key words

chromophore - oligonucleotide - building block - fluorescence - energy transfer

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References

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