Synthesis and evaluation of oligodeoxynucleotides containing acyclic nucleosides: introduction of three novel analogues and a summary.
Novel flexible oligodeoxynucleotides containing (S)-1-(2,3-dihydroxypropyl)thymine or 2',3'-seco-thymidine nucleoside analogues were synthesized on an automated DNA-synthesizer. Oligodeoxynucleotides with one, two or three acyclic nucleosides incorporated in the middle or in the ends of 17-mers have been evaluated. 3'-End-modified oligomers were significantly stabilized towards 3'-exonucleolytic degradation compared to unmodified analogues and showed acceptable hybridization properties as measured by UV experiments. For oligodeoxynucleotide analogues containing the three novel acyclic monomers in the middle, a more pronounced reduction in duplex stability was observed. All oligodeoxynucleotides containing acyclic nucleoside analogues made so far are evaluated with respect to stability towards 3'-exonucleolytic degradation and hybridization properties.
Nielsen
P
P
Department of Chemistry, Odense University, Denmark.
Dreiøe
L H
LH
Wengel
J
J
D001483:Base Sequence; D005092:Exonucleases / Q000378:metabolism; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009691:Nucleic Acid Denaturation; D009693:Nucleic Acid Hybridization; D009705:Nucleosides / Q000138:chemical synthesis*; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism
D009705:Nucleosides; D009838:Oligodeoxyribonucleotides; D005092:Exonucleases