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

ABSTRACT:

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

SUBMITTER: Svatunek D 

PROVIDER: S-EPMC5906496 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature