title: Protected maleimide building blocks for the decoration of peptides, peptoids, and peptide nucleic acids.
abstract: Monomers allowing for the introduction of [2,5-dimethylfuran]-protected maleimides into polyamides such as peptides, peptide nucleic acids, and peptoids were prepared, as well as the corresponding oligomers. Suitable maleimide deprotection conditions were established in each case. The stability of the adducts generated by Michael-type maleimide-thiol reaction and Diels-Alder cycloaddition to maleimide deprotection conditions was exploited to prepare a variety of conjugates from peptide and PNA scaffolds incorporating one free and one protected maleimide. The target molecules were synthesized by using two subsequent maleimide-involving click reactions separated by a maleimide deprotection step. Carrying out maleimide deprotection and conjugation simultaneously gave better results than performing the two reactions subsequently.
authors.affiliation: Departament de Química Orgànica and IBUB, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, 08028 Barcelona, Spain.
authors.forename: Xavier
authors.initials: X
authors.lastname: Elduque
authors.forename: Albert
authors.initials: A
authors.lastname: Sánchez
authors.forename: Kapil
authors.initials: K
authors.lastname: Sharma
authors.forename: Enrique
authors.initials: E
authors.lastname: Pedroso
authors.forename: Anna
authors.initials: A
authors.lastname: Grandas
mesh_terms: D003500:Cyclization; D008301:Maleimides / Q000138:chemical synthesis / Q000737:chemistry*; D009757:Nylons / Q000138:chemical synthesis / Q000737:chemistry; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D034444:Peptoids / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D008301:Maleimides; D009757:Nylons; D020135:Peptide Nucleic Acids; D010455:Peptides; D034444:Peptoids; C043592:maleimide