Exploiting Protected Maleimides to Modify Oligonucleotides, Peptides and Peptide Nucleic Acids

Molecules

Clément Paris¹  Omar Brun¹  Enrique Pedroso²  Anna Grandas¹ 

[1] Departament de Química Orgànica i IBUB, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, 08028 Barcelona, Spain;

关键词: protected maleimides;    oligonucleotides;    peptides;    conjugates;    cyclization;   

DOI  :  10.3390/molecules20046389

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.