DNA-based phosphane ligands.
In order to expand the repertoire of DNA sequences specifically interacting with transition metals, we report here the first examples of DNA sequences carrying mono- and bidentate phosphane ligands as well as P,N-ligands. Aminoalkyl-modified oligonucleotides have been reacted at predetermined internal sites with carboxylate derivatives of pyrphos, BINAP and phosphinooxazoline (PHOX) 2 b-d. Carbodiimide coupling in the presence of N-hydroxysuccinimide provided the DNA-ligand conjugates in 38-78 % yield. Phosphane-containing oligonucleotides and their phosphane sulfide analogues were characterized by mass spectrometry (MALDI-TOF and FT-ICR-ESI) and their stability after purification and isolation was systematically investigated. While DNA-appended pyrphos ligand was quickly oxidized, BINAP and PHOX conjugates showed high stabilities, making them useful precursors for incorporation of transition metals into DNA.
Caprioara
Mihaela
M
Institute of Pharmacy and Molecular Biotechnology, Ruprecht-Karls University Heidelberg, 69120 Heidelberg, Germany.
Fiammengo
Roberto
R
Engeser
Marianne
M
Jäschke
Andres
A
D001671:Biochemistry / Q000379:methods*; D002851:Chromatography, High Pressure Liquid; D004247:DNA / Q000737:chemistry*; D008024:Ligands; D010720:Phosphines / Q000737:chemistry*
D008024:Ligands; D010720:Phosphines; D004247:DNA; C044646:phosphine