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A convergent and cost-effective strategy to synthesize enantiospecific nucleoside/ nucleotide analogs from readily available α-amino acids has been described. Both (L)- and (D)-methionine were transformed in four steps to the corresponding key intermediates (L)- and (D)- 2-(tert-butyloxycarbonylamino)-4-bromomethyl butyrate. Nucleophilic displacement of the bromide by nucleic acid bases (e.g., adenine,...
The first solid-phase synthesis of novel peptide-derived enantiospecific nucleic acid analogs (PDNAs), employing all three stereoisomers of 4-(N 9 -adeninyl)-2-amino(t-boc)-butyric acid as ADNA (amino acid-derived nucleoside analogs) monomers has been described. The preliminary melting temperature (T m ) data obtained by hybridization experiments demonstrated that these PDNAs can anneal...