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Protected maleimide building blocks for the decoration of peptides, peptoids and peptide nucleic acids
Elduque Busquets, Xavier; Sánchez, Albert; Sharma, Kapil; Pedroso Muller, Enrique; Grandas Sagarra, Anna
Universitat de Barcelona
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.
Pèptids
Àcids nucleics
Oligòmers
Síntesi orgànica
Biotecnologia
Aminoàcids
Proteïnes
Peptides
Nucleic acids
Oligomers
Organic synthesis
Biotechnology
Amino acids
Proteins
(c) American Chemical Society , 2013
Article
info:eu-repo/semantics/acceptedVersion
American Chemical Society
         

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