Design And Synthesis Of An Azabicyclic Nucleoside Phosphoramidite For Oligonucleotide Antisense Constructs

Nucleosides, Nucleotides & Nucleic Acids
Juan C SalinasStephen Hanessian

Abstract

We report the synthesis and biophysical evaluation of an azabicycle dinucleotide with restricted γ, β, and ε torsion angles, featuring the introduction of a piperidine ring that locks the conformation of the nucleoside into an RNA-type nucleic acid. The conceptual basis of the design is predicated upon the notion that the conformation of the phosphate group linking two RNA nucleotides can be approximated with an azabicyclic phosphoramidite which may also benefit from a unique stereoelectronic effect.

References

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Jan 15, 2016·Organic & Biomolecular Chemistry·Robert D GiacomettiStephen Hanessian
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Methods Mentioned

BETA
thermal affinity
acetylation
column chromatography
NMR

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