A Tetrazine-Labile Vinyl Ether Benzyloxycarbonyl Protecting Group (VeZ): An Orthogonal Tool for Solid-Phase Peptide Chemistry

作者：Staderini Matteo; Gambardella Alessia; Lilienkampf Annamaria; Bradley Mark^*

来源：Organic Letters, 2018, 20(11): 3170-3173.

DOI：10.1021/acs.orglett.8b00898

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.

• 出版日期2018-6-1