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Issue 99, 2018
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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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Supplementary files

Article information


Submitted
12 Sep 2018
Accepted
20 Nov 2018
First published
21 Nov 2018

Chem. Commun., 2018,54, 14005-14008
Article type
Communication

Hydrophilic azaspiroalkenes as robust bioorthogonal reporters

P. An, H. Wu, T. M. Lewandowski and Q. Lin, Chem. Commun., 2018, 54, 14005
DOI: 10.1039/C8CC07432A

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