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Synthesis 2020; 52(20): 2962-2969
DOI: 10.1055/s-0040-1707194
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© Georg Thieme Verlag Stuttgart · New York

Selective Chemical Modification of DNA with Boronic Acids by On-Column CuAAc Reactions

Mégane Debiais
a   Institut des Biomolécules Max Mousseron, University of Montpellier, CNRS, ENCSM, Montpellier, France   Email: michael.smietana@umontpellier.fr
,
Jean-Jacques Vasseur
a   Institut des Biomolécules Max Mousseron, University of Montpellier, CNRS, ENCSM, Montpellier, France   Email: michael.smietana@umontpellier.fr
,
Sabine Müller
b   University Greifswald, Institute for Biochemistry, Greifswald, Germany
,
Michael Smietana∗
a   Institut des Biomolécules Max Mousseron, University of Montpellier, CNRS, ENCSM, Montpellier, France   Email: michael.smietana@umontpellier.fr
› Author AffiliationsThe Agence Nationale de la Recherche and the Deutsche Forschungsgemeinschaft are gratefully acknowledged for financial support (ANR PCRI ‘TEMPLAR’-16-CE92- 0010-01; DFG MU1396/11).
Further Information

Publication History

Received: 14 May 2020

Accepted after revision: 15 June 2020

Publication Date:
14 July 2020 (online)

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Abstract

The use of the Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) reaction for the preparation of oligonucleotide conjugates is by now familiar. However, the selective introduction of boronic acids into DNA and RNA sequences by CuAAC reactions has long been considered impossible due to the incompatibility of the boronic acid moiety with copper salts. Here we describe two new methods for the selective on-column functionalization of oligonucleotides with boronic acids via two different CuAAC reactions. The first one allows the introduction of a phenylboronic acid at the 5′-extremity of oligonucleotides, while the selective intrastrand positioning of the modification can be achieved with the second one. Both methods were applied to the DNA and RNA series (up to a 20-mer) with good isolated yields and excellent purities. These results illustrate the potential of the reported methods for selective incorporation of boronic acids into oligonucleotides.

Key words

CuAAc - boronic acid - oligonucleotide - bioconjugation - DNA - RNA

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707194.
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