Synthesis of amino-acid-derived nucleo(side/tide) analogs for peptide-derived enantiospecific nucleic acid analogs

A convergent and cost-effective strategy to synthesize enantiospecific nucleoside/nucleotide analogs from readily available alpha-amino acids has been described. Both (L)- and (D)-methionine were transformed in four steps to the corresponding key intermediates (L)- and (D)-2-(tertbutyloxycarbonylamino)-4-bromomethyl butyrate. Nucleophilic displacement of the bromide by nucleic acid bases (e.g., adenine, thymine, guanine, cytosine) provided the enantiomerically pure monomers required for the solid-phase synthesis of novel peptide-derived enantiospecific nucleic acid analogs. (C) 1996 Academic Press, Inc.