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DNA‐Based Phosphane Ligands
Author(s) -
Caprioara Mihaela,
Fiammengo Roberto,
Engeser Marianne,
Jäschke Andres
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200601058
Subject(s) - dna , chemistry , computational biology , combinatorial chemistry , biology , biochemistry
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.