4-Cyano-2-butenyl Group: A New Type of Protecting Group in Oligonucleotide Synthesis via Phosphoramidite Approach

Abstract

4-Cyano-2-butenyl (CB) is a new type of protecting group for the intemucleotidic bonds in the synthesis of oligodeoxyribonucleotides by the phosphoramidite approach. This group is stable to acidic conditions and can be removed under mild conditions by a δ-elimination pathway using aqueous ammonium hydroxide.

Notes

It is roughly estimated that for a systemic dosing for treatment of a chronic disease about 700 to 900 kilograms per year of drug is needed to meet the present demand

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We calculated the cost of manufacturing cyanoethyl and CB phosphoramidites at kilogram scales and found that the latter could be produced at approximately 60% of the cost of cyanoethyl amidite synthons.