A Genetically Encoded Multifunctional Unnatural Amino Acid for Versatile Protein Manipulations in Living Cells

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2017 Apr 29

PMID 28451140

Citations 29

Authors

Yun Ge

Xinyuan Fan

Peng R Chen

Affiliations

Soon will be listed here.

Abstract

The genetic code expansion strategy allowed incorporation of unnatural amino acids (UAAs) bearing diverse functional groups into proteins, providing a powerful toolkit for protein manipulation in living cells. We report a multifunctional UAA, --azidobenzyloxycarbonyl lysine (PABK), that possesses a panel of unique properties capable of fulfilling various protein manipulation purposes. In addition to being used as a bioorthogonal ligation handle, an infrared probe and a photo-affinity reagent, PABK was shown to be chemically decaged by -cyclooctenols a strain-promoted 1,3-dipolar cycloaddition, which provides a new bioorthogonal cleavage strategy for intracellular protein activation. The biocompatibility and efficiency of this method were demonstrated by decaging of a PABK-caged firefly luciferase under living conditions. We further extended this method to chemically rescue a bacterial toxin OspF inside mammalian host cells.

Citing Articles

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Cellular Site-Specific Incorporation of Noncanonical Amino Acids in Synthetic Biology.

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Cracking the Code: Reprogramming the Genetic Script in Prokaryotes and Eukaryotes to Harness the Power of Noncanonical Amino Acids.

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Evolution of Pyrrolysyl-tRNA Synthetase: From Methanogenesis to Genetic Code Expansion.

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A pyridinium-based strategy for lysine-selective protein modification and chemoproteomic profiling in live cells.

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