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PubMed · 7816642

Antisense pro-drugs: 5'-ester oligodeoxynucleotides.

N N Polushin·J S Cohen
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Abstract

Oligonucleotides bearing a terminal lipophilic group attached through a biodegradable ester bond should be useful as antisense pro-drugs with improved cellular uptake. The synthesis of 5'-ester oligonucleotides is, however, problematic due to lability of the ester bond during aqueous ammonia treatment that is commonly used for the deprotection of synthetic oligonucleotides. The synthesis of 5'-palmitoyl oligodeoxynucleotides was accomplished in good yield by the use of a combination of base-labile tert-butylphenoxyacetyl amino protecting groups (t-BPA), the oxalyl-CPG anchor group, and ethanolamine (EA) as a deprotecting reagent.

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AcylationBase SequenceEstersEthanolamineEthanolaminesMolecular Sequence DataOligodeoxyribonucleotidesOligonucleotides, AntisensePalmitatesProdrugsJournal ArticleResearch Support, Non-U.S. Gov't

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N N Polushin, J S Cohen. 1994-12-11. Antisense pro-drugs: 5'-ester oligodeoxynucleotides.. https://doi.org/10.1093/nar%2F22.24.5492

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