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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… Click to show full abstract
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.
Journal Title: Organic letters
Year Published: 2019
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