A novel phosphoramidite, N,N-diisopropylamino-2-cyanoethyl-9-anthracenemethyl phosphoramidite 1, was prepared and coupled with the terminal 5'-hydroxyl of support-bound T10 and the putative phosphite triester intermediate was subsequently reacted with iodine in the presence of either water or a series of primary and secondary amines. The reactivity of 1 compared to a previously reported benzyl phosphoramidite 2 was also investigated: oxidation of the product of coupling 2 with CPG-T10-5'OH under aqueous conditions resulted in greater than 30% of the benzyl moiety being retained. In contrast, essentially complete loss of the 9-anthracenemethyl group was observed using 1 under the same conditions. Oligonucleotides modified with a terminal phosphate monoester, lipophilic, fluorescent or cationic groups were thus prepared.
ASJC Scopus subject areas
- Organic Chemistry
- Drug Discovery
Cooke, L. A., Frauendorf, C., Gilea, M., Holmes, S. C., & Vyle, J. (2006). Solid-phase synthesis of terminal oligonucleotide-phosphoramidate conjugates. Tetrahedron Letters, 47(5), 719-722. https://doi.org/10.1016/j.tetlet.2005.11.098