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Issue 27, 2014
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Cap analogs containing 6-thioguanosine – reagents for the synthesis of mRNAs selectively photo-crosslinkable with cap-binding biomolecules

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Abstract

Numerous biomolecules recognize the 7-methylguanosine cap structure present at the 5′ ends of eukaryotic mRNAs. Photo-crosslinking is a valuable technique to study these interactions. We report three anti-reverse cap analogs containing a photo-activable nucleoside, 6-thioguanosine (6SG), that enable the synthesis of capped RNAs with 6SG positioned exclusively as the first transcribed nucleotide. The effect of the 6-thioguanosine moiety on binding to the translation factor eIF4E and the efficiency of mRNA translation was determined. The utility of mRNAs with a 6SG-modified cap in crosslinking experiments is shown by mapping the histone H4 cap-binding pocket.

Graphical abstract: Cap analogs containing 6-thioguanosine – reagents for the synthesis of mRNAs selectively photo-crosslinkable with cap-binding biomolecules

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Publication details

The article was received on 08 Jan 2014, accepted on 26 Mar 2014 and first published on 26 Mar 2014


Article type: Paper
DOI: 10.1039/C4OB00059E
Citation: Org. Biomol. Chem., 2014,12, 4841-4847
  • Open access: Creative Commons BY license
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    Cap analogs containing 6-thioguanosine – reagents for the synthesis of mRNAs selectively photo-crosslinkable with cap-binding biomolecules

    M. Nowakowska, J. Kowalska, F. Martin, A. d'Orchymont, J. Zuberek, M. Lukaszewicz, E. Darzynkiewicz and J. Jemielity, Org. Biomol. Chem., 2014, 12, 4841
    DOI: 10.1039/C4OB00059E

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