Facile Synthesis of N-(9-Fluorenylmethyloxycarbonyl)-3-amino-3-(4,5-dimethoxy-2-nitrophenyl)propionic Acid as a Photocleavable Linker for Solid-Phase Peptide Synthesis

Abstract

A photocleavable linker, N-(9-fluorenylmethyloxycarbonyl)-3-amino-3-(4,5-dimethoxy-2-nitrophenyl) propionic acid was synthesized from veratraldehyde, with simple reaction and separation steps. This linker was stable under the normal solid-phase peptide synthesis conditions and rearranged to a labile form when irradiated with UV light (lambda = 365 nm). A model peptide sequence (YGGFL) was synthesized and released from solid supports with high efficiency by UV irradiation.