Caged Cyclopropenes with Improved Tetrazine Ligation Kinetics

Abstract

Activatable cyclopropenes are unreactive toward their inverse electron demand Diels-Alder reaction partner (e.g., s-tetrazines) until they are activated. The activation strategy is highly modular due to the cyclopropene’s ability to be caged by various light- and enzyme-activatable groups. This work describes the next generation of activatable cyclopropenes with a new core scaffold that maintains the activation modularity of the first generation but improves upon the ligation kinetics with s-tetrazines by ≤270-fold.

Publication type
Publication
Organic Letters, 21(10), 3721-3725
Pratik Kumar
Pratik Kumar
Assistant Professor - Reader F
Omar Zainul
Omar Zainul
Undergraduate student
Frank M. Camarda
Frank M. Camarda
Undergraduate student
Ting Jiang
Ting Jiang
PhD student
John A. Mannone
John A. Mannone
Undergraduate student
Wei Huang
Wei Huang
PhD student