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The phosphoramidite monomer of the C-nucleoside 2'-aminoethoxy-2-amino-3-methylpyridine (AE-MAP) has been synthesized for the first time and incorporated into triplex-forming oligonucleotides (TFOs). Ultraviolet melting and DNase I footprinting studies show that AE-MAP is a potent triplex-stabilizing monomer that is selective for GC base pairs. TFOs containing AE-MAP bind with high affinity to duplexes but only weakly to single stranded DNA. In addition, AE-MAP confers high nuclease resistance on oligonucleotides. TFOs containing AE-MAP have potential for gene knock-out and gene expression studies.

Original publication

DOI

10.1002/chem.201102287

Type

Journal article

Journal

Chemistry

Publication Date

23/12/2011

Volume

17

Pages

14851 - 14856

Keywords

Base Pairing, Base Sequence, DNA, Enzyme Activation, Molecular Sequence Data, Oligonucleotides, Pyridines