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2′-modified oligoribonucleotides containing 1,2-diol and aldehyde groups. Synthesis and properties

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Abstract

1,2-Diol-oligoribonucleotides were prepared using fully protected 2′-O-[2-(2,3-dihydroxypropyl)amino-2-oxoethyl]uridine 3′-phosphoramidite. Incorporation of the modified uridine residue into oligonucleotide chains was not shown to significantly affect the thermal stability of RNA-RNA and RNA-DNA duplexes. Periodate oxidation of the 1,2-diol group resulted in reactive 2′-aldehyde oligoribonucleotides. These oligonucleotides were studied for their application in the affinity modification of RNA recognizing proteins with an example of bacterial ribonuclease P.

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Abbreviations

DMTr:

4,4′-dimethoxytrityl

Udao:

2′-O-[2-(2,3-dihydroxypropyl)amino-2-oxoethyl]uridine

Udap:

2′-O-(2,5-dioxo-3-azapentyl)uridine

MALDI-TOF MS:

Matrix-Assisted Laser Desorption Ioniziation-Time of Flight Mass Spectrometry

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Authors and Affiliations

  1. Chemistry department and A. N. Belozersky Institute of Physico-Chemical Biology, M.V. Lomonossov Moscow State University, 119991, Moscow, Leninskie gory, 1, Russia

    E. A. Khomyakova, E. M. Zubin, N. G. Dolinnaya, E. A. Kubareva & T. S. Oretskaya

  2. Philipps University, 35037, Marburg, Germany

    L. V. Pavlova & R. K. Hartmann

  3. Science Technology Information Centre, Moscow, Russia

    E. V. Kazanova

  4. Research Institute of Physical-Chemical Medicine, Moscow, Russia

    I. P. Smirnov & G. E. Pozmogova

  5. Ernst-Moritz-Arndt University, 17487, Greifswald, Germany

    S. Muller

Authors
  1. E. A. Khomyakova
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  2. E. M. Zubin
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  3. L. V. Pavlova
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  4. E. V. Kazanova
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  5. I. P. Smirnov
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  6. G. E. Pozmogova
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  7. S. Muller
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  8. N. G. Dolinnaya
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  9. E. A. Kubareva
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  10. R. K. Hartmann
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  11. T. S. Oretskaya
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Corresponding author

Correspondence to T. S. Oretskaya.

Additional information

Original Russian Text © E.A. Khomyakova, E.M. Zubin, L.V. Pavlova, E.V. Kazanova, I.P. Smirnov, G.E. Pozmogova, S. Muller, N.G. Dolinnaya, E.A. Kubareva, R.K. Hartmann, T.S. Oretskaya, 2012, published in Bioorganicheskaya Khimiya, 2012, Vol. 38, No. 5, pp. 555–568.

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Khomyakova, E.A., Zubin, E.M., Pavlova, L.V. et al. 2′-modified oligoribonucleotides containing 1,2-diol and aldehyde groups. Synthesis and properties. Russ J Bioorg Chem 38, 488–499 (2012). https://doi.org/10.1134/S1068162012050068

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  • DOI: https://doi.org/10.1134/S1068162012050068

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