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Selective functionalization at N2-position of guanine in oligonucleotides via reductive amination

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Abstract

Chemo- and site-specific modifications in oligonucleotides have wide applicability as mechanistic probes in chemical biology. However, methods that label specific sites in nucleic acids are scarce, especially for labeling DNA/RNA from biological or enzymatic sources rather than synthetic ones. Here we have employed a classical reaction, reductive amination, to selectively functionalize the N2-amine of guanosine and 2′-deoxyguanosine monophosphate (GMP/dGMP). This method specifically modifies guanine in DNA and RNA oligonucleotides, while leaving the other nucleobases unaffected. Using this approach, we have successfully incorporated a reactive handle chemoselectively into nucleic acids for further functionalization and downstream applications.

Graphical abstract: Selective functionalization at N2-position of guanine in oligonucleotides via reductive amination

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Article information


Submitted
12 Aug 2020
Accepted
15 Oct 2020
First published
15 Oct 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Selective functionalization at N2-position of guanine in oligonucleotides via reductive amination

B. A. Bhoge, P. Mala, J. S. Kurian, V. Srinivasan and I. Saraogi, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC05492E

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