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Synlett 2012; 23(17): 2435-2448
DOI: 10.1055/s-0032-1317158
DOI: 10.1055/s-0032-1317158
account
Organic Chemistry of DNA Functionalization; Chromophores as DNA Base Substitutes versus DNA Base/2′-Modifications
Further Information
Publication History
Received: 22 June 2012
Accepted after revision: 01 August 2012
Publication Date:
10 September 2012 (online)
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.
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