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Molecules 2015, 20(4), 6389-6408; doi:10.3390/molecules20046389

Exploiting Protected Maleimides to Modify Oligonucleotides, Peptides and Peptide Nucleic Acids

Departament de Química Orgànica i IBUB, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, 08028 Barcelona, Spain
These authors contributed equally to this work.
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Author to whom correspondence should be addressed.
Academic Editor: Scott Reed
Received: 12 February 2015 / Revised: 27 March 2015 / Accepted: 31 March 2015 / Published: 10 April 2015
(This article belongs to the Special Issue Bioconjugations)
View Full-Text   |   Download PDF [382 KB, uploaded 13 April 2015]   |  

Abstract

This manuscript reviews the possibilities offered by 2,5-dimethylfuran-protected maleimides. Suitably derivatized building blocks incorporating the exo Diels-Alder cycloadduct can be introduced at any position of oligonucleotides, peptide nucleic acids, peptides and peptoids, making use of standard solid-phase procedures. Maleimide deprotection takes place upon heating, which can be followed by either Michael-type or Diels-Alder click conjugation reactions. However, the one-pot procedure in which maleimide deprotection and conjugation are simultaneously carried out provides the target conjugate more quickly and, more importantly, in better yield. This procedure is compatible with conjugates involving oligonucleotides, peptides and peptide nucleic acids. A variety of cyclic peptides and oligonucleotides can be obtained from peptide and oligonucleotide precursors incorporating protected maleimides and thiols. View Full-Text
Keywords: protected maleimides; oligonucleotides; peptides; conjugates; cyclization protected maleimides; oligonucleotides; peptides; conjugates; cyclization
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Paris, C.; Brun, O.; Pedroso, E.; Grandas, A. Exploiting Protected Maleimides to Modify Oligonucleotides, Peptides and Peptide Nucleic Acids. Molecules 2015, 20, 6389-6408.

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