Synthesis and Hybridization Properties of Modified Oligonucleotides with PNA-DNA Dimer Blocks
- 1 July 1997
- journal article
- Published by Taylor & Francis in Nucleosides and Nucleotides
- Vol. 16 (7-9) , 977-980
- https://doi.org/10.1080/07328319708006120
Abstract
Different modified PNA-DNA dimer-analogous synthons (I and II) were synthesized as phosphoramidites. These dimer units were assembled by a 5′-modified deoxythymidine and a modified PNA monomer. These synthons were used in the routine coupling procedure for oligonucleotides. Therefore no PNA coupling chemistry is necessary to synthesize PNA-DNA chimeric oligonucleotides. Various deoxyoligonucleotides were synthesized introducing the dimer blocks I and II at different positions in the sequences. Melting temperatures of the modified oligonucleotides with their complementary DNA analogues were determined. Backbone modifications of oligonucleotides are required in the antisense strategy for protection against endonucleolytic cleavage in biological environment. Peptide nucleic acids (PNA fragments) are known to be nuclease resistant analogues, which show stable and discriminating hybridization. For this reason we prepared chimeric PNA-DNA oligomers by incorporation of two different modified PNA-DNA dimer blocks (Scheme A) into oligonucleotides. Melting temperatures of the modified oligonucleotides with their complementary DNA were determined.Keywords
This publication has 4 references indexed in Scilit:
- New approach to solid phase synthesis of polyamide nucleic acids analogues (PNA) and PNA-DNA conjugatesTetrahedron Letters, 1996
- Solid phase synthesis of directly linked PNA-DNA-hybridsTetrahedron Letters, 1995
- Synthesis of Peptide Nucleic Acid Monomers Containing the Four Natural Nucleobases: Thymine, Cytosine, Adenine, and Guanine and Their OligomerizationThe Journal of Organic Chemistry, 1994
- PNA hybridizes to complementary oligonucleotides obeying the Watson–Crick hydrogen-bonding rulesNature, 1993