Genetically Encoded Cyclopropene Directs Rapid, Photoclick Chemistry-Mediated Protein Labeling in Mammalian Cells

Genetic incorporation of a cyclopropene amino acid, Nε-(1-methylcycloprop-2-enecarboxamido)-lysine (CpK), into sperm whale myoglobin site-specifically in E. coli as well as enhanced green fluorescent protein in mammalian cells was achieved through amber codon suppression employing an orthogonal amin...

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Bibliographic Details
Published in:Angewandte Chemie International Edition
Main Authors: Yu, Zhipeng, Pan, Yanchao, Wang, Zhiyong, Wang, Jiangyun, Lin, Qing
Format: Text
Language:English
Published: 2012
Subjects:
Article
Sperm whale
Online Access:http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3517012
http://www.ncbi.nlm.nih.gov/pubmed/22997015
https://doi.org/10.1002/anie.201205352
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Summary:Genetic incorporation of a cyclopropene amino acid, Nε-(1-methylcycloprop-2-enecarboxamido)-lysine (CpK), into sperm whale myoglobin site-specifically in E. coli as well as enhanced green fluorescent protein in mammalian cells was achieved through amber codon suppression employing an orthogonal aminoacyl-tRNA synthetase/tRNACUA pair. Because of its high ring strain, cyclopropene exhibited fast reaction kinetics (up to 58 ± 16 M−1 s−1) in the photoclick reaction and allowed rapid (~ 2 min) bioorthogonal labeling of proteins in mammalian cells.

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