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On-resin Passerini reaction toward C-terminal photocaged peptides

So, Wing Ho and Xia, Jiang 2020. On-resin Passerini reaction toward C-terminal photocaged peptides. Organic Letters 22 (1) , pp. 214-218. 10.1021/acs.orglett.9b04182

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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 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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: American Chemical Society
ISSN: 1523-7060
Last Modified: 27 Sep 2022 01:06

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