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Anthraquinones may be incorporated into oligonucleotides by a variety of methods using a host of different phosphoramidites. The anthraquinone moiety is useful for applications such as intercalation, duplex and triplex stabilization, photochemical immobilization, quenching of fluorescence, electrochemical detection, and charge transport through nucleic acids. Barton and co-workers(1) have studied the importance of the tether in electronic coupling of the anthraquinone to the DNA. Connection of the anthraquinone moiety to the nucleobase of 2'-deoxyuridine via an ethynyl group provides an electronic coupling to the nucleobase pi-stack. Such nucleotides were made by incorporation of a 5-ethynyl-dU nucleotide using 5-Ethynyl-dU CEP (BA0167) followed by a post-synthetic palladium-catalyzed Sonogashira coupling with 2-iodoanthraquinone.1 For the direct incorporation of an ethynyl-dU-linked anthraquinone into an oligonucleotide, BA0309 may be used, avoiding post-synthetic palladium couplings.
- Gorodetsky, A. A.; Green, O.; Yavin, E.; Barton, J. K. Bioconjugate Chem. 2007, 18, 1434-1441.