Preparation and Properties of a New Type of Acyclic, Achiral Nucleoside Analogue

Preparation of the nucleoside analogues 1 and incorporation of 1, B = T, in deoxyribooligonucleotides by the phosphoramidite method is described. A two-step deprotection procedure was developed to reduce cleavage of the modified allylic unit. The binding properties of the modified oligonucleotides t...

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Bibliographic Details
Published in:Nucleosides, nucleotides & nucleic acids nucleotides & nucleic acids, 2003-10, Vol.22 (5-8), p.623-627
Main Authors: Boesen, Thomas, Sejer Pedersen, Daniel, Jensen, Jacob, Munck, Michael T., Nielsen, Brian M., Petersen, Asger B., Henriksen, Ulla, Dahl, Britta M., Dahl, Otto
Format: Article
Language:English
Subjects:
Antiviral agents
Binding Sites
DNA - chemistry
Indicators and Reagents
Modified oligonucleotides
Molecular Conformation
Nucleoside analogues
Nucleosides - chemical synthesis
Nucleosides - chemistry
Oligodeoxyribonucleotides - chemical synthesis
Oligodeoxyribonucleotides - chemistry
RNA - chemistry
Stereoisomerism
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Summary:Preparation of the nucleoside analogues 1 and incorporation of 1, B = T, in deoxyribooligonucleotides by the phosphoramidite method is described. A two-step deprotection procedure was developed to reduce cleavage of the modified allylic unit. The binding properties of the modified oligonucleotides towards complementary DNA and RNA has been evaluated by T m measurements showing a ΔT m of −2 to −6.5°C per modification. An oligonucleotide with two modifications at the 3′-end showed considerable resistance towards cleavage by a 3′-exonuclease. No antiviral activity against HIV-1 or HSV-1 was found for 1, B = G or T, or for any of the trihydroxy derivatives 5.
ISSN:1525-7770
1532-2335
DOI:10.1081/NCN-120021967