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Isocyanides: Promising Functionalities in Bioorthogonal Labeling of Biomolecules
Isocyanides have drawn increasing attention in biological applications due to their attractive properties and unique reactivities, which can undergo various reactions, such as multicomponent reactions, α-addition reactions, [4 + 1] cycloaddition reactions, and the reaction scope keeps expanding. In...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Frontiers Media S.A.
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8117350/ https://www.ncbi.nlm.nih.gov/pubmed/33996762 http://dx.doi.org/10.3389/fchem.2021.670751 |
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author | Zhu, Yuchen Liao, Jia-Yu Qian, Linghui |
author_facet | Zhu, Yuchen Liao, Jia-Yu Qian, Linghui |
author_sort | Zhu, Yuchen |
collection | PubMed |
description | Isocyanides have drawn increasing attention in biological applications due to their attractive properties and unique reactivities, which can undergo various reactions, such as multicomponent reactions, α-addition reactions, [4 + 1] cycloaddition reactions, and the reaction scope keeps expanding. In addition to acting as reactants for the preparation of structurally interesting and diverse N-heterocycles or peptidomimetics, this type of functionality may be a good choice in the labeling and modulation of biomolecules due to the high biocompatibility and small size to minimize modifications on the parent molecule. It has been demonstrated that isocyanides can participate in biomolecule labeling through three strategies, including the two-component bioorthogonal reaction, multicomponent reaction, and metal chelation. Among them, the isocyanide-tetrazine reaction has been better studied recently, augmenting the potency of isocyanide as a bioorthogonal handle. This review will focus on the recent progress in isocyanide chemistry for labeling of biomolecules. Meanwhile, methods to introduce isocyano groups into biomacromolecules are also described to facilitate wider applications of this unique functionality. |
format | Online Article Text |
id | pubmed-8117350 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | Frontiers Media S.A. |
record_format | MEDLINE/PubMed |
spelling | pubmed-81173502021-05-14 Isocyanides: Promising Functionalities in Bioorthogonal Labeling of Biomolecules Zhu, Yuchen Liao, Jia-Yu Qian, Linghui Front Chem Chemistry Isocyanides have drawn increasing attention in biological applications due to their attractive properties and unique reactivities, which can undergo various reactions, such as multicomponent reactions, α-addition reactions, [4 + 1] cycloaddition reactions, and the reaction scope keeps expanding. In addition to acting as reactants for the preparation of structurally interesting and diverse N-heterocycles or peptidomimetics, this type of functionality may be a good choice in the labeling and modulation of biomolecules due to the high biocompatibility and small size to minimize modifications on the parent molecule. It has been demonstrated that isocyanides can participate in biomolecule labeling through three strategies, including the two-component bioorthogonal reaction, multicomponent reaction, and metal chelation. Among them, the isocyanide-tetrazine reaction has been better studied recently, augmenting the potency of isocyanide as a bioorthogonal handle. This review will focus on the recent progress in isocyanide chemistry for labeling of biomolecules. Meanwhile, methods to introduce isocyano groups into biomacromolecules are also described to facilitate wider applications of this unique functionality. Frontiers Media S.A. 2021-04-29 /pmc/articles/PMC8117350/ /pubmed/33996762 http://dx.doi.org/10.3389/fchem.2021.670751 Text en Copyright © 2021 Zhu, Liao and Qian. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms. |
spellingShingle | Chemistry Zhu, Yuchen Liao, Jia-Yu Qian, Linghui Isocyanides: Promising Functionalities in Bioorthogonal Labeling of Biomolecules |
title | Isocyanides: Promising Functionalities in Bioorthogonal Labeling of Biomolecules |
title_full | Isocyanides: Promising Functionalities in Bioorthogonal Labeling of Biomolecules |
title_fullStr | Isocyanides: Promising Functionalities in Bioorthogonal Labeling of Biomolecules |
title_full_unstemmed | Isocyanides: Promising Functionalities in Bioorthogonal Labeling of Biomolecules |
title_short | Isocyanides: Promising Functionalities in Bioorthogonal Labeling of Biomolecules |
title_sort | isocyanides: promising functionalities in bioorthogonal labeling of biomolecules |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8117350/ https://www.ncbi.nlm.nih.gov/pubmed/33996762 http://dx.doi.org/10.3389/fchem.2021.670751 |
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