A Tetrazine-Labile Vinyl Ether Benzyloxycarbonyl Protecting Group (VeZ): An Orthogonal Tool for Solid-Phase Peptide Chemistry.
A Tetrazine-Labile Vinyl Ether Benzyloxycarbonyl Protecting Group (VeZ): An Orthogonal Tool for Solid-Phase Peptide Chemistry.
复制标题
四嗪不稳定的乙烯基醚苄氧基羰基保护基团 (VeZ)：固相肽化学的正交工具。
作者：
Matteo Staderini;A. Gambardella;Annamaria Lilienkampf;M. Bradley
通过逆电子需求狄尔斯-阿尔德反应用四嗪处理，选择性裂解乙烯基醚苄氧基羰基 (VeZ) 保护基。这代表了一种用于固相肽合成的新正交保护基团，Fmoc-Lys(VeZ)-OH 可作为 Fmoc-Lys(Alloc)-OH 和 Fmoc-Lys(Dde)-OH 的多功能替代品，如两种生物学相关环肽的合成所证明的那样。
The vinyl ether benzyloxycarbonyl (VeZ) protecting group is selectively cleaved by treatment with tetrazines via an inverse electron-demand Diels-Alder reaction. This represents a new orthogonal protecting group for solid-phase peptide synthesis, with Fmoc-Lys(VeZ)-OH as a versatile alternative to Fmoc-Lys(Alloc)-OH and Fmoc-Lys(Dde)-OH, as demonstrated by the synthesis of two biologically relevant cyclic peptides.