Nucleosides, Nucleotides & Nucleic Acids 2003-01-01

Nucleobase modified peptide nucleic acid.

R H E Hudson, R D Viirre, N McCourt, J Tse

Index: Nucleosides Nucleotides Nucleic Acids 22 , 1029-1033, (2003)

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Abstract

The Pd0/Cu1 catalyzed cross-coupling of terminal alkynes onto peptide nucleic acid monomers or submonomers bearing iodinated nucleobases has been utilized as a route to base-modified oligomers. Both 5-iodouracil and 5-iodocytosine derivatives undergo the cross-coupling to give the expected products in moderate to good yields. However, depending on the particular substrates and reaction conditions, the cross-coupling may be followed by a ring closing reaction to give the fluorescent furano- and pyrrolo-fused uracil and cytosine derivatives, respectively.