The synthesis 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 ). The APNA tetramer 18 was prepared from the
amino acid monomer (S)-1 using
classical
peptide synthesis. UV absorption spectra and 1H NMR
data of this tetramer suggested that base
stacking interactions in the APNA oligomers may be
favorable.
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.-The synthesis of the title thymidine (VIII) is achieved via stereoselective reduction of the keto acid (I) using Bacillus stearothermophilus lactate dehydrogenase. The dimer and tetramer of (VIII) are prepared by classical peptide synthesis. Spectroscopic data of the tetramer suggest that base stacking interactions in the aromatic peptide nucleic acid oligomers have positive effects on cell permeability and duplex stability. -(TSANTRIZOS, Y. S.; LUNETTA, J. F.; BOYD, M.; FADER, L. D.; WILSON, M.-C.; J. Org. Chem. 62 (1997) 16, 5451-5457; Dep. Chem. Biochem., Concordia Univ., Montreal, Que. H3G 1M8, Can.; EN)
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