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2′‐Aminoethoxy‐2‐amino‐3‐methylpyridine in Triplex‐Forming Oligonucleotides: High Affinity, Selectivity and Resistance to Enzymatic Degradation
Author(s) -
Lou Chenguang,
Shelbourne Montserrat,
Fox Keith R.,
Brown Tom
Publication year - 2011
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.201102287
Subject(s) - oligonucleotide , nuclease , footprinting , phosphoramidite , monomer , chemistry , dna , gene , enzyme , nucleoside , stereochemistry , biochemistry , microbiology and biotechnology , biology , polymer , organic chemistry , base sequence
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.