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oai:recercat.cat:2445/494232025-12-04T21:42:46Zcom_2072_1057col_2072_478917col_2072_478933

Protected maleimide building blocks for the decoration of peptides, peptoids and peptide nucleic acids Elduque Busquets, Xavier Sánchez-Moya, Albert Sharma, Kapil Pedroso Muller, Enrique Grandas Sagarra, Anna Pèptids Àcids nucleics Oligòmers Síntesi orgànica Biotecnologia Aminoàcids Proteïnes Peptides Nucleic acids Oligomers Organic synthesis Biotechnology Amino acids Proteins 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. 2014-02-05T09:00:14Z 2014-12-31T23:02:05Z 2013 2014-02-04T15:10:00Z info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion Versió postprint del document publicat a: http://dx.doi.org/10.1021/bc4000614 Bioconjugate Chemistry, 2013, vol. 24, num. 5, p. 832-839 http://dx.doi.org/10.1021/bc4000614 (c) American Chemical Society , 2013 info:eu-repo/semantics/openAccess American Chemical Society Articles publicats en revistes (Química Inorgànica i Orgànica)