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Functionalization of Mono‐ and Oligonucleotides with Phosphane Ligands by Amide Bond Formation
Author(s) -
Nuzzolo Marzia,
Grabulosa Arnald,
Slawin Alexandra M. Z.,
Meeuwenoord Nico J.,
van der Marel Gijsbert A.,
Kamer Paul C. J.
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000125
Subject(s) - chemistry , moiety , amide , oligonucleotide , nuclear magnetic resonance spectroscopy , peptide bond , surface modification , stereochemistry , combinatorial chemistry , organic chemistry , dna , biochemistry , enzyme
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, 31 P NMR spectrometry. Coordination of a phosphane‐modified 15‐mer to a [PdCl(η 3 ‐allyl)] moiety has been confirmed by 31 P NMR spectroscopy.