Orthogonal Protection of Peptides and Peptoids for Cyclization by the Thiol鈥揈ne Reaction and Conjugation

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• 作者：Xavier Elduque ; Enrique Pedroso ; Anna Grandas
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：April 4, 2014
• 年：2014
• 卷：79
• 期：7
• 页码：2843-2853
• 全文大小：472K
• 年卷期：v.79,no.7(April 4, 2014)
• ISSN：1520-6904

文摘

Cyclic peptides and peptoids were prepared using the thiol鈥揺ne Michael-type reaction. The linear precursors were provided with additional functional groups allowing for subsequent conjugation: an orthogonally protected thiol, a protected maleimide, or an alkyne. The functional group for conjugation was placed either within the cycle or in an external position. The click reactions employed for conjugation with suitably derivatized nucleoside or oligonucleotides were either cycloadditions (Diels鈥揂lder, Cu(I)-catalyzed azide鈥揳lkyne) or the same Michael-type reaction as for cyclization.