title: 2'-Aminoethoxy-2-amino-3-methylpyridine in triplex-forming oligonucleotides: high affinity, selectivity and resistance to enzymatic degradation.
abstract: 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.
authors: School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK.
authors: Chenguang
authors: C
authors: Lou
authors: Montserrat
authors: M
authors: Shelbourne
authors: Keith R
authors: KR
authors: Fox
authors: Tom
authors: T
authors: Brown
mesh_terms: D020029:Base Pairing; D001483:Base Sequence; D004247:DNA / Q000737:chemistry* / Q000378:metabolism*; D004789:Enzyme Activation / Q000187:drug effects*; D008969:Molecular Sequence Data; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism*; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: C571701:2'-aminoethoxy-2-amino-3-methylpyridine; D009841:Oligonucleotides; D011725:Pyridines; C051802:triplex DNA; D004247:DNA