Exploring the Potential of Norbornene‐Modified Mannosamine Derivatives for Metabolic Glycoengineering

Späte, Anne‐Katrin; Dold, Jeremias E. G. A.; Batroff, Ellen; Schart, Verena F.; Wieland, Daniel E.; Baudendistel, Oliver R.; Wittmann, Valentin

doi:10.1002/cbic.201600197

Cited by 33 publications

(38 citation statements)

References 68 publications

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“…This was attributed to low incorporation of the bulky norbornene structure. 205 206 and zebrafish 207 using bioorthogonal sugar derivatives. In one example, Bertozzi et al developed a bioorthogonal approach for systemic imaging of glycans by metabolically incorporating a BCN-functionalized sialic acid (BCNSia 1) at various development stages of Zebrafish, following by IEDDA labelling.…”

Section: Metabolically Incorporation For Glycan Modificationmentioning

confidence: 99%

“…Due to the orthogonality between IEDDA and azide-alkyne cycloaddition, most IEDDA-sugars may be used for dual labelling with Ac4GlcNAz. 106,107,117,199,200,205 In one example, Wittmann et al simultaneous incorporated cyclopropene and azide handles in cell surfaces and performed orthogonal dual labelling with a Tz dye and DIBO-488. 107 Despite the fast kinetics of IEDDA compared to SPAAC, longer incubation of Tz probes (3 hours for the norbornene sugar and 6 hours for terminal alkenes) was necessary for efficient staining due to low incorporation efficiency.…”

Section: Metabolically Incorporation For Glycan Modificationmentioning

confidence: 99%

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Inverse electron demand Diels–Alder reactions in chemical biology

2017

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The emerging inverse electron demand Diels-Alder (IEDDA) reaction stands out from other bioorthogonal reactions by virtue of its unmatchable kinetics, excellent orthogonality and biocompatibility. With the recent discovery of novel dienophiles and optimal tetrazine coupling partners, attention has now been turned to the use of IEDDA approaches in basic biology, imaging and therapeutics. Here we review this bioorthogonal reaction and its promising applications for live cell and animal studies. We first discuss the key factors that contribute to the fast IEDDA kinetics and describe the most recent advances in the synthesis of tetrazine and dienophile coupling partners. Both coupling partners have been incorporated into proteins for tracking and imaging by use of fluorogenic tetrazines that become strongly fluorescent upon reaction. Selected notable examples of such applications are presented. The exceptional fast kinetics of this catalyst-free reaction, even using low concentrations of coupling partners, make it amenable for in vivo radiolabelling using pretargeting methodologies, which are also discussed. Finally, IEDDA reactions have recently found use in bioorthogonal decaging to activate proteins or drugs in gain-of-function strategies. We conclude by showing applications of the IEDDA reaction in the construction of biomaterials that are used for drug delivery and multimodal imaging, among others. The use and utility of the IEDDA reaction is interdisciplinary and promises to revolutionize chemical biology, radiochemistry and materials science.

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Section: Metabolically Incorporation For Glycan Modificationmentioning

confidence: 99%

Section: Metabolically Incorporation For Glycan Modificationmentioning

confidence: 99%

Inverse electron demand Diels–Alder reactions in chemical biology

2017

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“…The same authors recently reported a series of norbornene‐tagged mannosamine derivatives suitable for metabolic engineering of glycan structures. They also demonstrated the dual‐colour labelling potential of these derivatives in combination with SPAAC chemistry …”

Section: Fluorescent Glycan Labelling Through Metabolic Engineeringmentioning

confidence: 96%

Bio‐orthogonal Fluorescent Labelling of Biopolymers through Inverse‐Electron‐Demand Diels–Alder Reactions

2017

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Bio‐orthogonal labelling schemes based on inverse‐electron‐demand Diels–Alder (IEDDA) cycloaddition have attracted much attention in chemical biology recently. The appealing features of this reaction, such as the fast reaction kinetics, fully bio‐orthogonal nature and high selectivity, have helped chemical biologists gain deeper understanding of biochemical processes at the molecular level. Listing the components and discussing the possibilities and limitations of these reagents, we provide a recent snapshot of the field of IEDDA‐based biomolecular manipulation with special focus on fluorescent modulation approaches through the use of bio‐orthogonalized building blocks. At the end, we discuss challenges that need to be addressed for further developments in order to overcome recent limitations and to enable researchers to answer biomolecular questions in more detail.

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“…We found that 43 % of all released sialic acids bear the acrylamide functionality (Figures S2 and S3); this demonstrates the high acceptance of this small reporter group by the enzymes. In comparison, mannosamine derivatives modified with a bulky norbornene were found to be incorporated with an efficiency of only 1 % . These findings also show that the acrylamide group is stable during metabolization and not attacked by thiols in a Michael‐type addition.…”

Section: Methodsmentioning

confidence: 99%

Triple Orthogonal Labeling of Glycans by Applying Photoclick Chemistry

et al. 2018

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Bioorthogonal labeling of multiple biomolecules is of current interest in chemical biology. Metabolic glycoengineering (MGE) has been shown to be an appropriate approach to visualizing carbohydrates. Here, we report that the nitrile imine–alkene cycloaddition (photoclick reaction) is a suitable ligation reaction in MGE. Using a mannosamine derivative with an acrylamide reporter group that is efficiently metabolized by cells and that quickly reacts in the photoclick reaction, we labeled sialic acids on the surface of living cells. Screening of several alkenes showed that a previously reported carbamate‐linked methylcyclopropene reporter that is well suited for the inverse‐electron‐demand Diels–Alder (DAinv) reaction has a surprisingly low reactivity in the photoclick reaction. Thus, for the first time, we were able to triply label glycans by a combination of DAinv, photoclick, and copper‐free click chemistry.

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Exploring the Potential of Norbornene‐Modified Mannosamine Derivatives for Metabolic Glycoengineering

Cited by 33 publications

References 68 publications

Inverse electron demand Diels–Alder reactions in chemical biology

Inverse electron demand Diels–Alder reactions in chemical biology

Bio‐orthogonal Fluorescent Labelling of Biopolymers through Inverse‐Electron‐Demand Diels–Alder Reactions

Triple Orthogonal Labeling of Glycans by Applying Photoclick Chemistry

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