Metabolic oligosaccharide engineering as a tool for glycobiology

Dube, Danielle H.; Bertozzi, Carolyn R.

doi:10.1016/j.cbpa.2003.08.006

Cited by 263 publications

(165 citation statements)

References 43 publications

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“…Metabolic sugar engineering, which inserts 'tags' into cellular glycoconjugates, has proven to be a powerful tool for the glycoproteomic analysis of a specific sugar modification [1][2][3] . This technique involves the incorporation of chemically modified sugars, such as azide-or alkyne-modified sugars, into cellular glycans via a normal biosynthetic pathway, and its subsequent detection with a probe, such as a FLAG-tag, biotin or fluorescent molecules [4][5][6] .…”

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confidence: 99%

Visualizing specific protein glycoforms by transmembrane fluorescence resonance energy transfer

et al. 2012

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Analyses of mice lacking glycosyltransferase have suggested that their pathological phenotypes are not attributable to the overall change of the sugar modification, but instead the result of changes of the glycan structures on a specific 'target' glycoprotein. Therefore, detecting or monitoring the glycosylation status of a specific protein in living cells is important, but no such methods are currently available. Here we demonstrate the detection of glycoforms of a specific glycoprotein using the fluorescence resonance energy transfer technique. using model proteins, we detect characteristic fluorescence resonance energy transfer signals from the specific glycoform-bearing target glycoprotein. We also show that, upon insulin removal, sialylated glycoforms of green fluorescent protein-tagged GLuT4 seem to be internalized more slowly than non-sialylated GLuT4. This novel analytical imaging tool allows studying the roles of specific glycan modifications of a protein of interest.

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confidence: 99%

Visualizing specific protein glycoforms by transmembrane fluorescence resonance energy transfer

et al. 2012

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“…Diese Methoden (die fast alle zur Einführung von Aziden in Biopolymere verwendet worden sind) umfassen, wie oben erwähnt, den Einbau nichtnatürlicher Gruppen mithilfe der zellulären Biosynthese, wie z. B. das metabolische Glycan-Engineering durch den nichtnatürlichen Kohlenhydratstoffwechsel, [166][167][168] die nichtnatürliche Proteintranslation, [169] die Exprimierung über auxotrophe Organismen, [170] die posttranslationale [171a,b] (Schema 23 B). [174] Darüber hinaus wurde eine RuCl 3 -vermittelte Variante mit hohen Ausbeuten für die Umsetzung auch sterisch gehinderter Azide beschrieben.…”

Section: Spurlose Staudinger-ligationunclassified

Chemoselektive Ligations‐ und Modifikationsstrategien für Peptide und Proteine

2008

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Die Untersuchung biologischer Fragestellungen mit chemischen Methoden wird meist als “Chemische Biologie” bezeichnet und setzt voraus, dass biologisch relevante Makromoleküle, wie Peptide und Proteine, chemisch zugänglich sind. Auf der Festphasensynthese von Peptiden aufbauend wurden viele chemoselektive Ligations‐ und Modifikationstechniken zur Verknüpfung synthetischer Peptide oder funktionaler Einheiten zu größeren synthetischen, biologisch relevanten Makromolekülen entwickelt. Dieser Aufsatz fasst die aktuellen Entwicklungen auf dem Gebiet der chemoselektiven Ligations‐ und Modifikationsstrategien zusammen und illustriert ihre Anwendbarkeit an Beispielen aus der chemischen Totalsynthese von Proteinen bis hin zur Semisynthese natürlicher modifizierter Proteine.

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“…It is of particular interest where on the cell-surface interacting human proteins are located and what their binding partners are. Bertozzi and coworkers have shown that functionalized carbohydrates can be incorporated into cells in vitro by active transporters and diffusion procedures [4,5]. She introduced the term bioorthogonal chemistry, which refers to any chemical reaction that can occur inside of living systems without interfering with native biochemical processes [6].…”

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confidence: 99%

Synthesis and application of water-soluble, photoswitchable cyanine dyes for bioorthogonal labeling of cell-surface carbohydrates

Mertsch

Letschert

Memmel

et al. 2016

Zeitschrift Für Naturforschung C

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Abstract:The synthesis of cyanine dyes addressing absorption wavelengths at 550 and 648 nm is reported. Alkyne functionalized dyes were used for bioorthogonal click reactions by labeling of metabolically incorporated sugar-azides on the surface of living neuroblastoma cells, which were applied to direct stochastic optical reconstruction microscopy (dSTORM) for the visualization of cellsurface glycans in the nm-range.

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Metabolic oligosaccharide engineering as a tool for glycobiology

Cited by 263 publications

References 43 publications

Visualizing specific protein glycoforms by transmembrane fluorescence resonance energy transfer

Visualizing specific protein glycoforms by transmembrane fluorescence resonance energy transfer

Chemoselektive Ligations‐ und Modifikationsstrategien für Peptide und Proteine

Synthesis and application of water-soluble, photoswitchable cyanine dyes for bioorthogonal labeling of cell-surface carbohydrates

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