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Hydrophilic azaspiroalkenes as robust bioorthogonal reporters

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Abstract

Two hydrophilic spiroalkenes, azaspiro[2.3]hex-1-ene and azaspiro[2.4]hept-1-ene, were designed and synthesized. Compared to the previously reported spiro[2.3]hex-1-ene, the azaspiroalkenes exhibited greater water solubility and reactivity as dipolarophiles in the photoinduced tetrazole–alkene cycloaddition reaction. In addition, an azaspiro[2.3]hex-1-ene-containing amino acid, AsphK, was found to be charged by an engineered pyrrolysyl-tRNA synthetase into proteins via amber codon suppression in E. coli as well as in mammalian cells.

Graphical abstract: Hydrophilic azaspiroalkenes as robust bioorthogonal reporters

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Publication details

The article was received on 12 Sep 2018, accepted on 20 Nov 2018 and first published on 21 Nov 2018


Article type: Communication
DOI: 10.1039/C8CC07432A
Citation: Chem. Commun., 2018, Advance Article
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    Hydrophilic azaspiroalkenes as robust bioorthogonal reporters

    P. An, H. Wu, T. M. Lewandowski and Q. Lin, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC07432A

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