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Readily Accessible Bicyclononynes for Bioorthogonal Labeling and Three‐Dimensional Imaging of Living Cells
Author(s) -
Dommerholt Jan,
Schmidt Samuel,
Temming Rinske,
Hendriks Linda J. A.,
Rutjes Floris P. J. T.,
van Hest Jan C. M.,
Lefeber Dirk J.,
Friedl Peter,
van Delft Floris L.
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201003761
Subject(s) - bioorthogonal chemistry , chemistry , glycan , cycloaddition , kinetics , in vitro , click chemistry , biophysics , combinatorial chemistry , biochemistry , biology , physics , quantum mechanics , glycoprotein , catalysis
I can see clearly now : Bicyclo[6.1.0]non‐4‐yne, an easily prepared, symmetrical cycloalkyne, displays excellent reaction kinetics in strain‐promoted cycloaddition reactions with azides and nitrones (see scheme). Highly specific protein modifications are demonstrated in vitro and subcellular‐resolved imaging of glycan expression was achieved in metastatic melanoma cells during invasive migration into three‐dimensional collagen lattices.