Progress towards a submonomer synthesis of peptide nucleic acid.
We report recent developments in the optimization of a submonomer synthesis of peptide nucleic acid based on the Fukuyama-Mitsunobu reaction. The key steps in the submonomer synthesis are the installation of an appropriately protected 2-aminoethyl group on the alpha-nitrogen of an amino acid and its subsequent acylation with a protected nucleobase derivative. The aggressive alkylation conditions require a scheme of maximal protection for the nucleobases and that is proposed herein for the pyrimidines.
Hudson
R H E
RH
Department of Chemistry, The University of Western Ontario, London, Ontario, Canada. rhhudson@uwo.ca
Viirre
R D
RD
D000596:Amino Acids; D003596:Cytosine / Q000737:chemistry; D007202:Indicators and Reagents; D009584:Nitrogen; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis*; D010720:Phosphines
D000596:Amino Acids; D007202:Indicators and Reagents; D020135:Peptide Nucleic Acids; D010720:Phosphines; D003596:Cytosine; C044646:phosphine; D009584:Nitrogen