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Updated: Jun 16, 2026

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology
Published on: May 15, 2012
Introducing azobenzenes as solid phase peptide synthesis linkers
Connor B Śmieja1, Lizun Xin1, Tianhui Tang1
1EaStCHEM School of Chemistry, University of Edinburgh David Brewster Rd Edinburgh EH9 3FJ UK Alison.Hulme@ed.ac.uk.
Abstract:
Orthogonally cleavable linkers are essential tools in solid-phase peptide synthesis (SPPS). We present a fluorogenic C̲o̲umarin-L̲oaded A̲z̲obenzene (COLAZ) linker for SPPS, which offers base and acid stability and a mild reductive cleavage. We synthesise model peptide WHISKEY with an integrated coumarin label using COLAZ resin and demonstrate that COLAZ and Rink linker technologies may be combined to produce peptides with a latent fluorophore. The biological compatibility of the COLAZ unit is demonstrated in vitro by tracking its glutathione-induced cleavage and in live cells by imaging the uptake of an R10 cell-penetrating peptide using two photon fluorescence (TPF) and stimulated Raman scattering (SRS).
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