Synthesis and Bioconjugation of Diene-Modified Oligonucleotides

The preparation of diene-modified oligonucleotides as well as their properties and further derivatization are described. Self-complementary oligonucleotides containing a diene moiety in the loop region form stable, hairpin-like secondary structures. These hairpin mimics can be further derivatized vi...

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Bibliographic Details
Published in:Bioconjugate chemistry 2005-07, Vol.16 (4), p.837-842
Main Authors: Tona, Rolf, Häner, Robert
Format: Article
Language:English
Subjects:
Chemical reactions
Chromatography, High Pressure Liquid
Chromatography, Thin Layer
Deoxyribonucleic acid
DNA
Hydrocarbons
Magnetic Resonance Spectroscopy
Models, Molecular
Oligonucleotides - chemical synthesis
Oligonucleotides - chemistry
Spectrometry, Mass, Electrospray Ionization
Spectrophotometry, Ultraviolet
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Summary:The preparation of diene-modified oligonucleotides as well as their properties and further derivatization are described. Self-complementary oligonucleotides containing a diene moiety in the loop region form stable, hairpin-like secondary structures. These hairpin mimics can be further derivatized via the Diels−Alder reaction. Diene modification in the stem region leads, in contrast, to a marked destabilization of the hairpin structure. No further reduction in stability is observed, however, upon conjugation of the stem-modified derivatives via the Diels−Alder reaction with an N-substituted maleimide dienophile.
ISSN:1043-1802
1520-4812
DOI:10.1021/bc050025t