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12.10.2020

+++ News Ticker Science #57 +++ Multicomponent Reaction +++

Isonitriles: Versatile Handles for the Bioorthogonal Functionalization of Proteins.

Due to their expertise in multicomponent reactions, Bernhard Westermann and Yanira Mendez have been invited to write a review for ACS Omega on isonitrile-initiated ligations of proteins. In their article, the authors summarize and critically comment on the recent findings in this field. Isonitriles are a key reactant in numerous multicomponent reactions, which are preferably applied for bioorthogonal coupling and labeling of biomolecules. Bioorthogonal chemical labeling enables in vivo protein localization or precisely targeted drug delivery. Bioorthogonal labeling has to take place under physiological conditions with fast kinetics, without affecting the native functional groups or being toxic to cellular processes. Since isonitriles do not naturally occur in proteins, the labeling reaction can only take place at the isonitrile-modified position in the protein. For this reason and due to other chemical properties, isonitriles are ideally suited for the bioorthogonal coupling of biomolecules.

At the IPB, isonitrile-based multi-component reactions (iMCRs) such as the Passerini 3-component reaction (condensation of an isonitrile, a carbonyl component and a carboxylic acid) and the Ugi 4-component reaction (with an additional amine) have been and are being intensively investigated and successfully applied. They have been proven to be extremely efficient for various syntheses, for example for the assembly of cyclic peptides as well as of lipo- and glyco-peptides. The conjugation of large biomolecules such as proteins and polysaccharides has also been recently achieved with iMCRs. With their review, the authors emphasize the great potential of isonitrile modification for protein ligation, imaging and many other applications and the low cost of these technologies.

Reference:
Yanira Méndez, Aldrin V. Vasco, Ana R. Humpierre & Bernhard Westermann. Isonitriles: Versatile Handles for the Bioorthogonal Functionalization of Proteins. ACS Omega 2020, https://doi.org/10.1021/acsomega.0c03728

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