Issue 27, 2014

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

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

Supplementary files

Article information

Article type
Paper
Submitted
08 Jan 2014
Accepted
26 Mar 2014
First published
26 Mar 2014
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2014,12, 4841-4847

Author version available

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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