Stereoselective synthesis of a thymine derivative of (S)-2-hydroxy-4-(2-aminophenyl)butanoic acid. A novel building block for the synthesis of aromatic peptidic nucleic acid oligomers

摘要

The sythesis of a thymine derivative of (S)-2-hydroxy-4-(2-aminophenyl)butanoic acid, compound 1, was achieved in high enantiomeric purity. The acyclic pyrimidine analog (S)-1 is a useful building block for the synthesis of a novel class of oligomers, the aromatic peptide nucleic acids (APNA, Scheme 1). The APNA tetramer 18 was prepared from the amino acid monomer (S)-1 using classical Peptide synthesis. UV absorption spectra and ~1Hd NMR data of this tetramer suggested that base Stacking interactions in the APNA oligomers may be favorable.