Readily Accessible Strained Difunctionalized trans-Cyclooctenes with Fast Click and Release Capabilities.

ABSTRACT: The click reaction between a functionalized trans-cyclooctene (TCO) and a tetrazine (Tz) is a compelling method for bioorthogonal conjugation in combination with payload releasing capabilities. However, the synthesis of difunctionalized TCOs remains challenging. As a result, these compounds are poorly accessible, which impedes the development of novel applications. In this work, the scalable and accessible synthesis of a new bioorthogonal difunctionalized TCO is reported in only four single selective high yielding steps starting from commercially available compounds. The TCO-Tz click reaction was assessed and revealed excellent kinetic rates and subsequently payload release was shown with various functionalized derivatives. Tetrazine triggered release of carbonate and carbamate payloads wa

SUBMITTER: Sondag D 

PROVIDER: S-EPMC10107714 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature