Protected Maleimide Building Blocks for the Decoration of Peptides, Peptoids, and Peptide Nucleic Acids

详细信息    查看全文

• 作者：Xavier Elduque ; Albert S谩nchez ; Kapil Sharma ; Enrique Pedroso ; Anna Grandas
• 刊名：Bioconjugate Chemistry
• 出版年：2013
• 出版时间：May 15, 2013
• 年：2013
• 卷：24
• 期：5
• 页码：832-839
• 全文大小：412K
• 年卷期：v.24,no.5(May 15, 2013)
• ISSN：1520-4812

文摘

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鈥搕hiol reaction and Diels鈥揂lder 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.