Substituted cyclopropenes serve as compact biorthogonal appendages that enable analysis of biomolecules in complex systems. Neurotransmitters, a chemically diverse group of biomolecules that control neuron excitation and inhibition, are not among the systems that have been studied using biorthogonal chemistry. Here we describe:1. Synthesis of cyclopropene-containing analogs of the excitatory amino acid neurotransmitter glutamate2. Synthesis of a photoactivatable version of cyclopropene-glutamate3. Bioorthogonal reaction of such cyclopropene-glutamates with tetrazines and tetrazoles
This strategy has the potential to permit deployment of cyclopropene-modified glutamate as a bioorthogonal probe of the neurotransmitter glutamate in vivo with spatiotemporal precision.
- Stable Cyclopropene-Containing Analogs of the Amino Acid Neurotransmitter Glutamate
- A Photocaged, Cyclopropene-Containing Analog of the Amino Acid Neurotransmitter Glutamate
- Caged Cyclopropenes with Improved Tetrazine Ligation Kinetics
- Modular Activatable Bioorthogonal Reagents
- Modular Enzyme- and Light-Based Activation of Cyclopropene-Tetrazine Ligation