Nucleobase modified peptide nucleic acid.
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.
Hudson
R H E
RH
Department of Chemistry, The University of Western Ontario, London, Ontario, Canada. rhhudson@uwo.ca
Viirre
R D
RD
McCourt
N
N
Tse
J
J
D001665:Binding Sites; D003432:Cross-Linking Reagents; D003596:Cytosine / Q000031:analogs & derivatives* / Q000737:chemistry; D007202:Indicators and Reagents; D007700:Kinetics; D015394:Molecular Structure; D020135:Peptide Nucleic Acids / Q000737:chemistry*; D014498:Uracil / Q000031:analogs & derivatives* / Q000737:chemistry
D003432:Cross-Linking Reagents; D007202:Indicators and Reagents; D020135:Peptide Nucleic Acids; C100034:iodouracil; C008143:5-iodocytosine; D014498:Uracil; D003596:Cytosine