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Issue 4, 2017
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Expanding a fluorescent RNA alphabet: synthesis, photophysics and utility of isothiazole-derived purine nucleoside surrogates

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Abstract

A series of emissive ribonucleoside purine mimics, all comprised of an isothiazolo[4,3-d]pyrimidine core, was prepared using a divergent pathway involving a key Thorpe–Ziegler cyclization. In addition to an adenosine and a guanosine mimic, analogues of the noncanonical xanthosine, isoguanosine, and 2-aminoadenosine were also synthesized and found to be emissive. Isothiazolo 2-aminoadenosine, an adenosine surrogate, was found to be particularly emissive and effectively deaminated by adenosine deaminase. Competitive studies with adenosine deaminase with each analogue in combination with native adenosine showed preference for the native substrate while still deaminating the isothiazolo analogues.

Graphical abstract: Expanding a fluorescent RNA alphabet: synthesis, photophysics and utility of isothiazole-derived purine nucleoside surrogates

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Publication details

The article was received on 06 Dec 2016, accepted on 26 Jan 2017 and first published on 30 Jan 2017


Article type: Edge Article
DOI: 10.1039/C6SC05354H
Citation: Chem. Sci., 2017,8, 2983-2993
  • Open access: Creative Commons BY-NC license
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    Expanding a fluorescent RNA alphabet: synthesis, photophysics and utility of isothiazole-derived purine nucleoside surrogates

    A. R. Rovira, A. Fin and Y. Tor, Chem. Sci., 2017, 8, 2983
    DOI: 10.1039/C6SC05354H

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