A Stable Precursor for Bioorthogonally Removable 3-Isocyanopropyloxycarbonyl (ICPrc) Protecting Groups

Synlett DOI: 10.1055/s-0040-1707220 Studies have established 3-isocyanopropyloxycarbonyl (ICPrc) moieties as bioorthogonally removable protecting groups. However, reagents to prepare ICPrc-protected amines are unstable, which critically limits the practical implementation of this chemistry. Here we report 3-isocyanopropyl (pentafluorophenyl) carbonates as bench-stable precursors for the synthesis of ICPrc-protected primary and secondary amines. The utility of the chemistry for bioconjugation applications is demonstrated by reversibly masking a lysine residue on a bioactive peptide. [...] © Georg Thieme Verlag Stuttgart · New YorkArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synlett - July 30, 2020 Category: Chemistry Authors: Tu, Julian Xu, Minghao Franzini, Raphael M. Tags: letter Source Type: research