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ChemComm
Page 4 of 5
DOI: 10.1039/C8CC00179K
COMMUNICATION
Journal Name
Judkins, C. W. am Ende, T. E. Ballard, Y. Fang, K. Riccardi, L. Di, E.
R. Guilmette, J. W. Schwartz, J. M. Fox and D. S. Johnson, Am
Chem Soc., 2015, 137, 11461; For reviews, see: (f) E. M. Sletten and C.
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conditions, demonstrating the bioorthogonality of this
method.12,14
J.
.
.
The novel Staudinger ligation was also applicable to
chemical modification of proteins in living cells (Fig. 5). For
example, the cell surface-specific fluorescent labeling was
achieved by the expression of transmembrane domain-fused
HaloTag protein on the cell surface, in which HaloTag is
present outside the cells, followed by the treatment with azido-
HaloTag ligand (14) and TESRA-phosphine (15) (Fig. 5A).
Notably, our Staudinger ligation method was also effective for
fluorescent labeling of HaloTag fused with NUP133 nuclear
pore complex protein (Fig. 5B). This result indicated that this
method could be used for chemical modification of intracellular
biomolecules. Indeed, compared with the fluorescent labeling
method using SPAAC modification with a dibenzo-fused
cyclooctyne possessing a TESRA moiety,12 our Staudinger
ligation method showed a superior result in terms of the
labeling efficiency inside the cells.
In summary, we have demonstrated that the Staudinger
reaction of 2,6-dichlorophenyl azide derivatives with
triarylphosphines proceeds rapidly to form robust aza-ylides.
The method allows for the efficient chemical modification of
proteins in living cells.
This work was supported by AMED under Grant Numbers
JP18am0101098 (Platform Project for Supporting Drug
Discovery and Life Science Research), JP18am0301024 (Basic
Science and Platform Technology Program for Innovative
Biological Medicine); the Cooperative Research Project of
Research Center for Biomedical Engineering; JSPS KAKENHI
Grant Numbers 15H03118 and 18H02104 (B; T.H.), 16H01133
and 18H04386 (Middle Molecular Strategy; T.H.), 17H06414
(Organelle Zone; T.H.), 26350971 (C; S.Y.), 18J11113 (JSPS
Research Fellow; T.M.); Naito Foundation (S.Y.).
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Conflicts of interest
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There are no conflicts to declare.
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4 | Chem. Commun., 201X, 00, 1-4
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