Application of the Inverse-Electron-Demand Diels-Alder Reaction for Metabolic Glycoengineering
The inverse electron-demand Diels-Alder (IEDDA or DAinv) reaction is an emerging bioorthogonal ligation reaction that finds application in all areas of chemistry and chemical biology. In this review we highlight its application in metabolic glycoengineering (MGE). MGE is a versatile tool to introduc...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Frontiers Media S.A.
2021-04-01
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| Series: | Frontiers in Chemistry |
| Subjects: | |
| Online Access: | https://www.frontiersin.org/articles/10.3389/fchem.2021.654932/full |
| _version_ | 1818850592431276032 |
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| author | Lisa Maria Haiber Markus Kufleitner Valentin Wittmann |
| author_facet | Lisa Maria Haiber Markus Kufleitner Valentin Wittmann |
| author_sort | Lisa Maria Haiber |
| collection | DOAJ |
| description | The inverse electron-demand Diels-Alder (IEDDA or DAinv) reaction is an emerging bioorthogonal ligation reaction that finds application in all areas of chemistry and chemical biology. In this review we highlight its application in metabolic glycoengineering (MGE). MGE is a versatile tool to introduce unnatural sugar derivatives that are modified with a chemical reporter group into cellular glycans. The IEDDA reaction can then be used to modify the chemical reporter group allowing, for instance, the visualization or isolation of glycoconjugates. During the last years, many different sugar derivatives as well as reporter groups have been published. These probes are summarized, and their chemical and biological properties are discussed. Furthermore, we discuss examples of MGE and subsequent IEDDA reaction that highlight its suitability for application within living systems. |
| first_indexed | 2024-12-19T06:51:35Z |
| format | Article |
| id | doaj.art-c45f445fa809433e849a5aac7ccd1e7a |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-12-19T06:51:35Z |
| publishDate | 2021-04-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-c45f445fa809433e849a5aac7ccd1e7a2022-12-21T20:31:41ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462021-04-01910.3389/fchem.2021.654932654932Application of the Inverse-Electron-Demand Diels-Alder Reaction for Metabolic GlycoengineeringLisa Maria HaiberMarkus KufleitnerValentin WittmannThe inverse electron-demand Diels-Alder (IEDDA or DAinv) reaction is an emerging bioorthogonal ligation reaction that finds application in all areas of chemistry and chemical biology. In this review we highlight its application in metabolic glycoengineering (MGE). MGE is a versatile tool to introduce unnatural sugar derivatives that are modified with a chemical reporter group into cellular glycans. The IEDDA reaction can then be used to modify the chemical reporter group allowing, for instance, the visualization or isolation of glycoconjugates. During the last years, many different sugar derivatives as well as reporter groups have been published. These probes are summarized, and their chemical and biological properties are discussed. Furthermore, we discuss examples of MGE and subsequent IEDDA reaction that highlight its suitability for application within living systems.https://www.frontiersin.org/articles/10.3389/fchem.2021.654932/fullinverse-electron-demand Diels-Alder reactioncarbohydratesmetabolic engineeringbioorthogonal chemistrytetrazines |
| spellingShingle | Lisa Maria Haiber Markus Kufleitner Valentin Wittmann Application of the Inverse-Electron-Demand Diels-Alder Reaction for Metabolic Glycoengineering Frontiers in Chemistry inverse-electron-demand Diels-Alder reaction carbohydrates metabolic engineering bioorthogonal chemistry tetrazines |
| title | Application of the Inverse-Electron-Demand Diels-Alder Reaction for Metabolic Glycoengineering |
| title_full | Application of the Inverse-Electron-Demand Diels-Alder Reaction for Metabolic Glycoengineering |
| title_fullStr | Application of the Inverse-Electron-Demand Diels-Alder Reaction for Metabolic Glycoengineering |
| title_full_unstemmed | Application of the Inverse-Electron-Demand Diels-Alder Reaction for Metabolic Glycoengineering |
| title_short | Application of the Inverse-Electron-Demand Diels-Alder Reaction for Metabolic Glycoengineering |
| title_sort | application of the inverse electron demand diels alder reaction for metabolic glycoengineering |
| topic | inverse-electron-demand Diels-Alder reaction carbohydrates metabolic engineering bioorthogonal chemistry tetrazines |
| url | https://www.frontiersin.org/articles/10.3389/fchem.2021.654932/full |
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