title: Exploiting protected maleimides to modify oligonucleotides, peptides and peptide nucleic acids.
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.
authors: Departament de Química Orgànica i IBUB, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, 08028 Barcelona, Spain. clementparis@ub.edu.
authors: Clément
authors: C
authors: Paris
authors: Departament de Química Orgànica i IBUB, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, 08028 Barcelona, Spain. o.brun@ub.edu.
authors: Omar
authors: O
authors: Brun
authors: Departament de Química Orgànica i IBUB, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, 08028 Barcelona, Spain. epedroso@ub.edu.
authors: Enrique
authors: E
authors: Pedroso
authors: Departament de Química Orgànica i IBUB, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, 08028 Barcelona, Spain. anna.grandas@ub.edu.
authors: Anna
authors: A
authors: Grandas
mesh_terms: D057930:Click Chemistry; D003500:Cyclization; D008301:Maleimides / Q000737:chemistry*; D009841:Oligonucleotides / Q000737:chemistry*; D020135:Peptide Nucleic Acids / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000737:chemistry
chemical_list: D008301:Maleimides; D009841:Oligonucleotides; D020135:Peptide Nucleic Acids; D010455:Peptides; D010456:Peptides, Cyclic