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ChemInform Abstract: 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.

✍ Scribed by Y. S. TSANTRIZOS; J. F. LUNETTA; M. BOYD; L. D. FADER; M.-C. WILSON

Publisher: John Wiley and Sons
Year: 2010
Weight: 36 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199802229

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✦ Synopsis

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.

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