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 acid s has been described. Both (L)- and (D)-methionine were transformed in four steps to the corresponding key intermediates (L)- and (D)-2-(ter tbutyloxycarbonylamino)-4-bromomethyl butyrate. Nucleophilic displacem ent of the bromide by nucleic acid bases (e.g., adenine, thymine, guan ine, cytosine) provided the enantiomerically pure monomers required fo r the solid-phase synthesis of novel peptide-derived enantiospecific n ucleic acid analogs. (C) 1996 Academic Press, Inc.