A mild and efficient solid-support synthesis of novel oligonucleotide conjugates

Bioconjugate Chemistry
I HabusS Agrawal

Abstract

Conjugates of oligodeoxyribonucleotide phosphorothioate (ODN-PS) with folic acid, retinoic acid, arachidonic acid, and methoxypoly(ethylene glycol)propionic acid have been synthesized. The procedure involved the initial solid-phase preparation of 5'-amino-functionalized ODN-PS using N-pent-4-enoyl-derived (PNT) nucleoside phosphoramidites followed by conjugation of the oligonucleotide either to the ligand acids, using 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide as a coupling reagent, or to their corresponding succinimidyl derivatives. Subsequent exposure of the support to aqueous ammonium hydroxide (28%, 2 h, 55 degrees C) resulted in the release of the fully deprotected ODN conjugates, which were purified by reversed-phase HPLC or by preparative polyacrylamide gel electrophoresis. The identity of the oligonucleotide conjugates was confirmed by MALDI-TOF mass spectral analysis.

References

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Citations

Jan 4, 2007·Journal of Materials Science. Materials in Medicine·Kaustubh D BhaleraoAlfred B O Soboyejo
Feb 4, 2021·Nucleic Acid Therapeutics·William F KiesmanGary Held
Jun 30, 2001·The Journal of Organic Chemistry·J T Hwang, M M Greenberg

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