Novel methodology for the preparation and purification of oligonucleotides incorporating phosphorothiolate termini

S. Battaggia, Joseph Vyle

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

A novel phosphoramidite; N,N-diisopropylamino-2-cyanoethyl-ortho-methylbenzylphosphoramidite 1, was prepared. The reaction of 1 with DMTrT and subsequent derivatisation of the phosphite triester product under solution-phase, Michaelis–Arbuzov conditions was investigated. Coupling of 1 with the terminal hydroxyl groups of support-bound oligodeoxyribonucleotides and subsequent reaction with an activated disulfide yielded oligonucleotides bearing a terminal, phosphorothiolate-linked, lipophilic moiety. The oligomers were readily purified using RP-HPLC. Silver(I)-mediated cleavage of the phosphorothiolate linkage and desalting of the oligonucleotides were performed readily in one step to yield cleanly the corresponding phosphate monester-terminated oligomers.
Original languageEnglish
Pages (from-to)861-863
Number of pages3
JournalTetrahedron Letters
Volume44
Issue number4
DOIs
Publication statusPublished - 20 Jan 2003

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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