Metabolic Glycan Imaging by Isonitrile–Tetrazine Click Chemistry
Open Access
- 13 May 2013
- journal article
- research article
- Published by Wiley in ChemBioChem
- Vol. 14 (9) , 1063-1067
Abstract
Seeing the sugar coating: N-Acetyl-glucosamine and mannosamine derivatives tagged with an isonitrile group are metabolically incorporated into cell-surface glycans and can be detected with a fluorescent tetrazine. This bioorthogonal isonitrile–tetrazine ligation is also orthogonal to the commonly used azide-cyclooctyne ligation, and so will allow simultaneous detection of the incorporation of two different sugars.Keywords
This publication has 47 references indexed in Scilit:
- Bioorthogonal Reaction Pairs Enable Simultaneous, Selective, Multi‐Target ImagingAngewandte Chemie International Edition, 2011
- Development and evaluation of new cyclooctynes for cell surface glycan imaging in cancer cellsChemical Science, 2011
- Biocompatible Copper(I) Catalysts for in Vivo Imaging of GlycansJournal of the American Chemical Society, 2010
- Bioorthogonal Chemistry: Fishing for Selectivity in a Sea of FunctionalityAngewandte Chemie International Edition, 2009
- Imaging the glycomeProceedings of the National Academy of Sciences, 2009
- Tetrazine-Based Cycloadditions: Application to Pretargeted Live Cell ImagingBioconjugate Chemistry, 2008
- Tetrazine Ligation: Fast Bioconjugation Based on Inverse-Electron-Demand Diels−Alder ReactivityJournal of the American Chemical Society, 2008
- Copper-free click chemistry for dynamic in vivo imagingProceedings of the National Academy of Sciences, 2007
- Imaging Cell Surface Glycans with Bioorthogonal Chemical ReportersJournal of the American Chemical Society, 2007
- Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cellsProceedings of the National Academy of Sciences, 2007