Metabolisches Glykoengineering mit <i>N</i>‐Acyl‐Seiten‐ ketten‐modifizierten Mannosaminen

Wratil, Paul R.; Horstkorte, Rüdiger; Reutter, Werner

doi:10.1002/ange.201601123

Cited by 29 publications

(2 citation statements)

References 439 publications

(482 reference statements)

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“…Similar low labeling efficiencyo fN-acetylglucosamine (GlcNAc) derivatives was also observed by others.I t has been speculated that this effect is the result of restriction of GlcNAc in the sialic acid pathway and the ability of GlcNAc analogues to produce multiple metabolic products. [21][22][23] Fluorescence microscopy was furthermore used to image the labeled cells.For this,A549 cells were first incubated with 4a at 0.29 mm for 3days and then treated with P 2h -BSA-FITC for 1, 5, 10, 15, or 30 min. Thegreen fluorescence that resulted from P 2h -BSA-FITC was clearly seen on the cells ( Figure 5).…”

Section: Angewandte Chemiementioning

confidence: 99%

Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction

et al. 2017

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We report a fast Staudinger reaction between perfluoroaryl azides (PFAAs) and aryl phosphines, occurring readily under ambient conditions. A rate constant as high as 18 M−1 s−1 was obtained between methyl 4-azido-2,3,5,6-tetrafluorobenzoate and methyl 2-(diphenylphosphanyl)benzoate in CD3CN/D2O. In addition, the iminophosphorane product was stable toward hydrolysis and aza-phosphonium ylide reactions. The PFAA-Staudinger reaction proved to be an excellent bioothorgonal reaction. PFAA-derivatized mannose and galactose were successfully transformed into cell surface glycans and efficiently labeled with phosphine-derivatized fluorescent bovine serum albumin.

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Section: Angewandte Chemiementioning

confidence: 99%

Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction

et al. 2017

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“…Then, the second bioorthogonal component (usually dibenzocyclooctyne DBCO or azadibenzocyclooctyne ADIBO) reacts with the azide reporter through click bioorthogonal chemistry. The DBCO/ADIBO component can be attached to a fluorescent dye, prodrug or targeting peptide for labelling and imaging, targeted drug release or enhanced targeting profile, respectively [25,137–139] …”

Section: Targeting Mechanismsmentioning

confidence: 99%

In Vivo Applications of Bioorthogonal Reactions: Chemistry and Targeting Mechanisms

Mitry

Greco

Osborn

2023

Chemistry A European J

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Bioorthogonal chemistry involves selective biocompatible reactions between functional groups that are not normally present in biology. It has been used to probe biomolecules in living systems, and has advanced biomedical strategies such as diagnostics and therapeutics. In this review, the challenges and opportunities encountered when translating in vitro bioorthogonal approaches to in vivo settings are presented, with a focus on methods to deliver the bioorthogonal reaction components. These methods include metabolic bioengineering, active targeting, passive targeting, and simultaneously used strategies. The suitability of bioorthogonal ligation reactions and bond cleavage reactions for in vivo applications is critically appraised, and practical considerations such as the optimum scheduling regimen in pretargeting approaches are discussed. Finally, we present our own perspectives for this area and identify what, in our view, are the key challenges that must be overcome to maximise the impact of these approaches.

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Dehydrogenation of the NH−NH Bond Triggered by Potassium tert‐Butoxide in Liquid Ammonia

et al. 2016

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A novel strategy for the dehydrogenation of the NH À NH bond is disclosed using potassium tert-butoxide (tBuOK) in liquid ammonia (NH 3 ) under air at room temperature. Its synthetic value is well demonstrated by the highly efficient synthesis of aromatic azo compounds (up to 100 % yield, 3 min), heterocyclic azo compounds, and dehydrazination of phenylhydrazine. The broad application of this strategy and its benefit to chemical biology is proved by a novel, convenient, one-pot synthesis of aliphatic diazirines, which are important photoreactive agents for photoaffinity labeling.

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Metabolisches Glykoengineering mit N‐Acyl‐Seiten‐ ketten‐modifizierten Mannosaminen

Cited by 29 publications

References 439 publications

Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction

Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction

In Vivo Applications of Bioorthogonal Reactions: Chemistry and Targeting Mechanisms

Dehydrogenation of the NH−NH Bond Triggered by Potassium tert‐Butoxide in Liquid Ammonia

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