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Synthesis and evaluation of oligodeoxynucleotides containing acyclic nucleosides: Introduction of three novel analogues and a summary

Authors
Journal
Bioorganic & Medicinal Chemistry
0968-0896
Publisher
Elsevier
Publication Date
Volume
3
Issue
1
Identifiers
DOI: 10.1016/0968-0896(94)00143-q

Abstract

Abstract 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.

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