On-Resin Passerini Reaction toward C-Terminal Photocaged Peptides.

Published in: Organic letters (2019)

An on-resin, three-component Passerini reaction was developed to synthesize C-terminal photocaged peptides. Highly compatible with conventional Fmoc SPPS, this reaction produces peptides with a C-terminal o-amido-6-nitroveratryl (αANV) ester in one pot with conserved chirality. Under physiological conditions, the C-terminal αANV ester rapidly photolyzed to revert to carboxylate, offering a convenient method for optical control of cellular signals by modulating the C-terminal carboxylate.

Keyphrases

amino acid
high resolution
transcription factor
signaling pathway
electron transfer
high speed
walled carbon nanotubes