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Chemical name: 1-Azido-12-chloro-3,6-dioxadodecane // Synonyms: 1-(2-(2-Azidoethoxy)ethoxy)-6-chlorohexane
|Molecular weight:||249,74 g/mol|
This chloroalkane linker serves as ligand for a specific modified bacterial haloalkane dehalogenase. This is a reporter protein whose sequence can easily be fused to a gene of interest. The reaction between the chloroalkane linker and the enzyme is fast and irreversible under physiological conditions and the system has been used extensively to measure protein-protein interactions in cells.
Furthermore, the additional azide moiety serves clickable moiety.
HaloTag technology: a versatile platform for biomedical applications; C. G. England, H. Luo and W. Cai; Bioconjug Chem 2015; 26: 975-86. https://doi.org/10.1021/acs.bioconjchem.5b00191.
HaloTag: a novel protein labeling technology for cell imaging and protein analysis; G. V. Los, L. P. Encell, M. G. McDougall, D. D. Hartzell, N. Karassina, C. Zimprich, M. G. Wood, R. Learish, R. F. Ohana, M. Urh, D. Simpson, J. Mendez, K. Zimmerman, P. Otto, G. Vidugiris, J. Zhu, A. Darzins, D. H. Klaubert, R. F. Bulleit and K. V. Wood; ACS Chem Biol 2008; 3: 373-382. https://doi.org/10.1021/cb800025k.
HaloTag-Targeted Sirtuin-Rearranging Ligand (SirReal) for the Development of Proteolysis-Targeting Chimeras (PROTACs) against the Lysine Deacetylase Sirtuin 2 (Sirt2); M. Schiedel, A. Lehotzky, S. Szunyogh, J. Oláh, S. Hammelmann, N. Wössner, D. Robaa, O. Einsle, W. Sippl, J. Ovádi, M. Jung; ChemBioChem 2020; 21(23): 3371-3376. https://doi.org/10.1002/cbic.202000351.
Selection of DNA-Encoded Libraries to Protein Targets within and on Living Cells; B. Cai, D. Kim, S. Akhand, Y. Sun, R. J. Cassell, A. Alpsoy, E. C. Dykhuizen, R. M. Van Rijn, M. K. Wendt, C. J. Krusemark; J. Am. Chem. Soc. 2019; 141(43): 17057-17061. https://doi.org/10.1021/jacs.9b08085.
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