Solid-phase synthesis of terminal oligonucleotide-phosphoramidate conjugates

L.A. Cooke, Christian Frauendorf, Manuela Gilea, S.C. Holmes, Joseph Vyle

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Abstract

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.
Original languageEnglish
Pages (from-to)719-722
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number5
DOIs
Publication statusPublished - 30 Jan 2006

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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