Chemistry for the synthesis of nucleobase-modified peptide nucleic acid
R. H. E. Hudson, R. D. Viirre, Y. H. Liu, F. Wojciechowski, and A. K. Dambenieks
Department of Chemistry, The University of Western
Ontario, London, Ontario N6A 5B7, Canada
Abstract: Peptide nucleic acid (PNA) presents a versatile scaffold
for chemical modifications that may benefit its solubility and hybridization
properties, conjugation chemistry, cell membrane permeability, and so
forth. We have employed straightforward chemical methods for the synthesis
of PNA monomers containing C5-or C6-modified pyrimidines.The C5-modified
pyrimidines are based on 5-hydroxymethyl-uracil or cytosine, or are
achieved by cross-coupling from the 5-iodonucleobase derivatives, while
C6 modifications are accessed from 6-carboxyuracil (orotic acid). We
have also developed an on-resin activation/conversion of uracil-containing
PNA oligomers to N4-cytosine-containing derivatives.
*Lecture presented at the symposium "Chemistry of nucleic acids", as part of the 39th IUPAC Congress and 86th Conference of the Canadian Society for Chemistry: Chemistry at the Interfaces, Ottawa, Canada, 10-15 August 2003. Other Congress presentations are published in this issue, pp. 1295-1603.
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