Elduque Xavier, Pedroso Enrique, Grandas Anna
Departament de Química Orgànica i IBUB, Facultat de Química, Universitat de Barcelona , Martí i Franquès 1-11, 08028 Barcelona, Spain.
J Org Chem. 2014 Apr 4;79(7):2843-53. doi: 10.1021/jo500427c. Epub 2014 Mar 21.
Cyclic peptides and peptoids were prepared using the thiol-ene 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-Alder, Cu(I)-catalyzed azide-alkyne) or the same Michael-type reaction as for cyclization.
使用硫醇-烯迈克尔型反应制备环肽和类肽。线性前体带有额外的官能团以便后续偶联：一个正交保护的硫醇、一个保护的马来酰亚胺或一个炔烃。用于偶联的官能团位于环内或外部位置。用于与适当衍生化的核苷或寡核苷酸偶联的点击反应要么是环加成反应（狄尔斯-阿尔德反应、铜（I）催化的叠氮化物-炔烃反应），要么是与环化反应相同的迈克尔型反应。
