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  • Title: Homo-N-oligonucleotides (N1/N9-C1' methylene bridge oligonucleotides): nucleic acids with left-handed helicity.
    Author: Ishiyama K, Smyth GE, Ueda T, Masutomi Y, Ohgi T, Yano J.
    Journal: J Am Chem Soc; 2004 Jun 23; 126(24):7476-85. PubMed ID: 15198594.
    Abstract:
    Oligonucleotides containing a methylene bridge between N1 or N9 of the heterocyclic base and C1' of the pentofuranosyl ring (homo-N-oligonucleotides) were synthesized. Melting curves revealed that such homo-type oligomers could cross-pair with complementary homo-type or natural oligomers. Circular-dichroic studies provide evidence that the homo-type dimers have a left-handed stacked conformation and further suggest that single-stranded and double-stranded homo-type oligomers adopt a left-handed conformation, while duplexes with natural oligomers or nucleic acids form RNA-like right-handed helices. NMR spectroscopy (NOESY) provides supporting evidence for a left-handed stacked conformation of the homo-type dimer, while atomic force microscopy indicates a left-handed helical conformation of homo-type dsDNA. Homo-type dimers and oligomers showed high resistance to digestion by snake-venom and calf-spleen phosphodiesterases and nuclease S1.
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