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Genetic encoding of 2-aryl-5-carboxytetrazole-based protein photo-cross-linkers

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Abstract

Three γ-heteroatom-substituted N-methylpyrroletetrazole-lysines (mPyTXKs) were synthesized and subsequently incorporated into proteins site-specifically via genetic code expansion. The γ-seleno-substituted derivative, mPyTSeK, showed excellent incorporation efficiency in Escherichia coli and allowed site-selective photo-cross-linking of the GST dimer. Furthermore, the mPyTSeK-cross-linked GST dimer can be cleaved under mild oxidative conditions. The incorporation of mPyTXKs into proteins in mammalian cells was also demonstrated. Lastly, the recombinantly expressed mPyTSeK-encoded Grb2 was shown to covalently capture its interaction partner, EGFR, in mammalian cell lysate, which was subsequently released after treatment with H2O2.

Graphical abstract: Genetic encoding of 2-aryl-5-carboxytetrazole-based protein photo-cross-linkers

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Publication details

The article was received on 27 Mar 2018, accepted on 06 Apr 2018 and first published on 06 Apr 2018


Article type: Communication
DOI: 10.1039/C8CC02431F
Citation: Chem. Commun., 2018, Advance Article
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    Genetic encoding of 2-aryl-5-carboxytetrazole-based protein photo-cross-linkers

    Y. Tian and Q. Lin, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC02431F

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