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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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.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Chemistry
Publisher:	American Chemical Society
ISSN:	1523-7060
Last Modified:	27 Sep 2022 01:06
URI:	https://orca.cardiff.ac.uk/id/eprint/141496

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