A computational model to predict the Diels–Alder reactivity of aryl/alkyl-substituted tetrazines

ABSTRACT: The tetrazine ligation is one of the fastest bioorthogonal ligations and plays a pivotal role in time-critical in vitro and in vivo applications. However, prediction of the reactivity of tetrazines in inverse electron demand Diels–Alder-initiated ligation reactions is not straight-forward....

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Detalles Bibliográficos
Autores principales: Svatunek, Dennis, Denk, Christoph, Mikula, Hannes
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Vienna 2017
Materias:
Original Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5906496/
https://www.ncbi.nlm.nih.gov/pubmed/29681659
http://dx.doi.org/10.1007/s00706-017-2110-x
Descripción
Sumario:ABSTRACT: The tetrazine ligation is one of the fastest bioorthogonal ligations and plays a pivotal role in time-critical in vitro and in vivo applications. However, prediction of the reactivity of tetrazines in inverse electron demand Diels–Alder-initiated ligation reactions is not straight-forward. Commonly used tools such as frontier molecular orbital theory only give qualitative and often even wrong results. Applying density functional theory, we have been able to develop a simple computational method for the prediction of the reactivity of aryl/alkyl-substituted tetrazines in inverse electron demand Diels–Alder reactions. GRAPHICAL ABSTRACT: [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s00706-017-2110-x) contains supplementary material, which is available to authorized users.

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