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A Tetrazine-Labile Vinyl Ether Benzyloxycarbonyl Protecting Group (VeZ): An Orthogonal Tool for Solid-Phase Peptide Chemistry
Organic Letters ( IF 5.2 ) Pub Date : 2018-05-23 00:00:00 , DOI: 10.1021/acs.orglett.8b00898
Matteo Staderini 1 , Alessia Gambardella 1 , Annamaria Lilienkampf 1 , Mark Bradley 1
Affiliation  

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.

中文翻译:

四嗪不稳定的乙烯基醚苄氧羰基保护基(VeZ):固相肽化学的正交工具

乙烯基醚苄氧基羰基(VeZ)保护基可通过反电子需求的Diels-Alder反应用四嗪处理选择性地裂解。这代表了固相肽合成的一个新的正交保护基,Fmoc-Lys(VeZ)-OH是Fmoc-Lys(Alloc)-OH和Fmoc-Lys(Dde)-OH的多用途替代品,合成两个生物学上相关的环肽。
更新日期:2018-05-23
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