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. 1994 Dec 11;22(24):5492–5496. doi: 10.1093/nar/22.24.5492

Antisense pro-drugs: 5'-ester oligodeoxynucleotides.

N N Polushin 1, J S Cohen 1
PMCID: PMC332106  PMID: 7816642

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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Selected References

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