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. 2008;47(12):2253-5.
doi: 10.1002/anie.200705456.

Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast huisgen cycloadditions

Xinghai Ning  1 , Jun Guo, Margreet A Wolfert, Geert-Jan Boons
Affiliations

Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast huisgen cycloadditions

Xinghai Ning et al. Angew Chem Int Ed Engl. 2008.
No abstract available

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Figures

Figure 1
Figure 1
Reagents for labeling of azido-containing biomolecules.
Figure 2
Figure 2
Metal free cycloadditons of compound 3 with azido-containing amino acid and saccharides.
Figure 3
Figure 3
Cell surface labeling with compounds 2 and 9. Jurkat cells grown for 3 days in the absence or presence of Ac4ManNAz (25 μM) were incubated (a) with compounds 2 and 9 (30 μM) for 0 – 180 min or (b) with compounds 2 and 9 (0 – 100 μM) for 1 h at room temperature. Next, cells were incubated with avidin-FITC for 15 min at 4°C, after which cell lysates were assessed for fluorescence intensity. Samples are indicated as follows: blank cells incubated with 2 (○) or 9 (□) and Ac4ManNAz cells incubated with 2 (●) or 9 (■). AU indicates arbitrary fluorescence units.
Figure 4
Figure 4
Fluorescence images of cells labeled with compound 9 and avidin-Alexa fluor 488. CHO cells grown for 3 days in the absence (d – f) or presence (a – c) of Ac4ManNAz (100 μM) were incubated with compound 9 (30 μM) for 1 h at 4°C (a, d) or room temperature (b, c, e, f). Next, cells were incubated with avidin-Alexa fluor 488 for 15 min at 4°C and, after washing, fixing, and staining for the nucleus with TO-PRO, imaged (a, b, d, e) or after washing incubated for 1 h at 37°C before fixing, nucleus staining, and imaging (c, f).
Scheme 1
Scheme 1
Reagents and conditions. a) TBSCl, pyridine; b) Br2, CHCl3; c) LDA, THF; d) 4-nitrophenyl chloroformate, pyridine, DCM; e) DMF, Et3N.
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