Fmoc-SPPS-compatible p-methoxyphenacyl-modified glutamic for the synthesis of photocaged peptides

Abstract

The development of photocaged glutamic acid (Glu) contributes to the time-resolved control of peptide and protein activities. Here, we efficiently synthesized the Glu with the side chain modified by photosensitive p-methoxyphenacyl group. This photocaged Glu can be introduced into peptide through standard 9‑fluorenylmethoxycarbonyl (Fmoc) solid phase peptide synthesis (SPPS), and can be re-exposed the Glu side-chain carboxy group by removing the photosensitive group under light irradiation. We prepared caged Endothelin-1 (ET-1) analogues with p-methoxyphenacyl-modified Glu and successfully achieved decaging.