Functionalization of Mono- and Oligonucleotides with Phosphane Ligands by Amide Bond Formation

Marzia Nuzzolo, Arnald Grabulosa, Alexandra M. Z. Slawin, Nico J. Meeuwenoord, Gijsbert A. van der Marel, Paul C. J. Kamer

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

Seven phosphane-functionalized deoxyuridines have been prepared by amide bond formation between aminodeoxyuridines and phosphanylcarboxylic acids. X-ray crystal structures for two of these new modified nucleosides have been obtained. The same coupling method has been extended to oligonucleotides. The phosphane containing strands have been purified and characterized by MALDI-TOF and, for the first time, P-31 NMR spectrometry. Coordination of a phosphane-modified 15-mer to a [PdCl(eta(3)-allyl)] moiety has been confirmed by P-31 NMR spectroscopy.

Original languageEnglish
Pages (from-to)3229-3236
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number17
DOIs
Publication statusPublished - Jun 2010

Keywords

  • Nucleosides
  • Olieonucleotides
  • DNA
  • Phosphanes
  • Palladium
  • ARTIFICIAL METALLOENZYMES
  • ASYMMETRIC CATALYSIS
  • ENANTIOSELECTIVE CATALYSIS
  • NUCLEIC-ACIDS
  • NUCLEOSIDES
  • EVOLUTION
  • LINKER

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