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Hydrophilic azaspiroalkenes as robust bioorthogonal reporters
Peng An1, Hsuan-Yi Wu, Tracey M Lewandowski
1Department of Chemistry, State University of New York at Buffalo, Buffalo, New York 14260, USA. qinglin@buffalo.edu.
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.
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