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5-Ethynyl-dU CE-Phosphoramidite

5-Ethynyl-dU CE-Phosphoramidite

CAS No.:615288-66-9

Phosphoramidite used to replace thymidine residues in oligonucleotides, for duplex stabilization.
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Replacement of thymidine residues with 5-ethynyl-dU residues results in duplex stabilization. The degree of stabilization is less than that observed with propynyl-dU residues.(1) Oligonucleotides with 5-ethynyl residues may also be used in transition metal-catalyzed coupling reactions. Two ethynyl-bearing oligonucleotides can be homo-coupled via a diyne linkage using copper catalysis. Further, the ethynyl groups may be used in copper-catalyzed couplings with arylacetylenes bearing anthraquinone, biotin, or fluorescein appendages.(2) Palladium catalyzed cross-coupling of ethynyl-dU-bearing oligonucleotidies with 2-iodoanthraquinone provides anthraquinone-bearing nucleic acids useful in electrochemical applications of DNA.(3)


  1. Graham, D.; Parkinson, J. A.; Brown, T. J. Chem. Soc, Perkin Trans. 1, 1998, 1131-1138.
  2. Minakawa, N.; Ono, Y.; Matsuda, A. J. Am. Chem. Soc. 2003, 125, 11545-11552.
  3. Gorodetsky, A. A.; Green, O.; Yavin, E.; Barton, J. K. Bioconjugate Chem. 2007, 18, 1434-1441.

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