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Issue 1, 2011
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Synthesis and hybridization properties of 2′-O-methylated oligoribonucleotides incorporating 2′-O-naphthyluridines

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Abstract

2′-O-(1-Naphthyl)uridine and 2′-O-(2-naphthyl)uridine were synthesized by a microwave-mediated reaction of 2,2′-anhydrouridine with naphthols. Using the 3′-phosphoramidite building blocks, these 2′-O-aryluridine derivatives were incorporated into 2′-O-methylated oligoribonucleotides. Incorporation of five 2′-O-(2-naphthyl)uridines into a 2′-O-methylated RNA sense strand significantly increased the thermostability of the duplex with a 2′-O-methylated RNA antisense strand. Circular dichroism spectroscopy and molecular dynamic simulation of the duplexes formed between the modified RNAs and 2′-O-methyl RNAs suggested that there are π–π interactions between two neighboring naphthyl groups in a sequence of the five consecutively modified nucleosides.

Graphical abstract: Synthesis and hybridization properties of 2′-O-methylated oligoribonucleotides incorporating 2′-O-naphthyluridines

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Publication details

The article was received on 12 Jun 2010, accepted on 08 Sep 2010 and first published on 29 Oct 2010


Article type: Paper
DOI: 10.1039/C0OB00248H
Citation: Org. Biomol. Chem., 2011,9, 210-218
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    Synthesis and hybridization properties of 2′-O-methylated oligoribonucleotides incorporating 2′-O-naphthyluridines

    M. Sekine, Y. Oeda, Y. Iijima, H. Taguchi, A. Ohkubo and K. Seio, Org. Biomol. Chem., 2011, 9, 210
    DOI: 10.1039/C0OB00248H

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