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Title: Exploiting protected maleimides to modify oligonucleotides, peptides and peptide nucleic acids
Author: Paris, Clément
Brun, Omar
Pedroso Muller, Enrique
Grandas Sagarra, Anna
Keywords: Pèptids
Àcids nucleics
Nucleic acids
Issue Date: 10-Apr-2015
Publisher: MDPI
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.
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It is part of: Molecules, 2015, vol. 20, p. 6389-6408
Related resource:
ISSN: 1420-3049
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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