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

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http://pubs.acs.org/doi/10.1021/acs.orglett.8b00898
Original languageEnglish
Pages (from-to)3170-3173
JournalOrganic letters
Volume20
Issue number11
Early online date23 May 2018
DOIs
Publication statusPublished - 1 Jun 2018

Abstract

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 for the synthesis of cyclic peptides, as demonstrated by the synthesis of melanotan II (MTII) and a constrained BAD BH3 peptide analogue.

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