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Title: Protected maleimide building blocks for the decoration of peptides, peptoids and peptide nucleic acids
Author: Elduque Busquets, Xavier
Sánchez-Moya, Albert
Sharma, Kapil
Pedroso Muller, Enrique
Grandas Sagarra, Anna
Keywords: Pèptids
Àcids nucleics
Síntesi orgànica
Nucleic acids
Organic synthesis
Amino acids
Issue Date: 2013
Publisher: American Chemical Society
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.
Note: Versió postprint del document publicat a:
It is part of: Bioconjugate Chemistry, 2013, vol. 24, num. 5, p. 832-839
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ISSN: 1043-1802
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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