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The stereoselective synthesis of a novel aromatic peptide nucleic acid (APNA) oligomer

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The stereoselective synthesis of a novel aromatic peptide nucleic acid (APNA) oligomer

Lunetta, Jacqueline F (1997) The stereoselective synthesis of a novel aromatic peptide nucleic acid (APNA) oligomer. Masters thesis, Concordia University.

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Abstract

The synthesis of the thymine derivative (S)-50, was achieved in high enantiomeric purity (98% ee). The (R) enhanced enantiomer was also synthesized with moderate enantiomeric purity (46% ee). This acyclic pyrimidine analog ((S)-50) is a useful building block for the synthesis of a novel class of oligomers, the aromatic peptide nucleic acids (APNA). The APNA tetramer 70 was prepared from the amino acid monomer (S)-50 using classical peptide synthesis. Chemical shift differences between the $\sp1$H NMR of monomer (S)-57 and tetramer 70 were observed which suggested that base stacking interactions in the oligomers may be favorable.

Divisions:Concordia University > Faculty of Arts and Science > Chemistry and Biochemistry
Item Type:Thesis (Masters)
Authors:Lunetta, Jacqueline F
Pagination:xiii, 95 leaves : ill. ; 29 cm.
Institution:Concordia University
Degree Name:Theses (M.Sc.)
Program:Chemistry and Biochemistry
Date:1997
Thesis Supervisor(s):Tsantrizos, Youla S
ID Code:225
Deposited By:Concordia University Libraries
Deposited On:27 Aug 2009 13:10
Last Modified:08 Dec 2010 10:13
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