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Issue 33, 2012
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Capping of oligonucleotides with “clickable” m3G-CAPs

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The RNA components of small nuclear ribonucleoproteins (U snRNPs) possess a characteristic 5′-terminal 2,2,7-trimethyl-guanosine CAP structure (m3G-CAP). This cap is an important component of the nuclear localization signal of U snRNPs. Here we report synthesis of four m3G-CAP constructs and the effective attachment of these onto oligonucleotides (ONs) using Cu(I) [3 + 2] cycloaddition (“click chemistry”). The four constructs (1–4, Fig. 1) are equipped with a handle that in principle allows for universal conjugation to any cargo and differ in their complexity starting from m3GpppA(linker) to m3GpppA(OMe)U(OMe)A(linker) that resembles the native m3G-CAP followed by the 2′-O-methylated sequence AUA. The four m3G-CAP containing constructs are equipped with an azide linker and by taking advantage of initial attachment of a novel activated triple bond donor p-aminomethyltoluic acid (PATA) to ONs on solid support we were able to synthesize novel bioconjugates equipped with different constructs carrying the m3G-CAP Nuclear Localisation Signal (NLS) for the investigation of nuclear delivery.

Graphical abstract: Capping of oligonucleotides with “clickable” m3G-CAPs

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Publication details

The article was received on 28 Sep 2012, accepted on 19 Oct 2012 and first published on 08 Nov 2012

Article type: Paper
DOI: 10.1039/C2RA22345G
RSC Adv., 2012,2, 12949-12962

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    Capping of oligonucleotides with “clickable” m3G-CAPs

    M. Honcharenko, J. Romanowska, M. Alvira, M. Jezowska, M. Kjellgren, C. I. Edvard Smith and R. Strömberg, RSC Adv., 2012, 2, 12949
    DOI: 10.1039/C2RA22345G

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