1451095-01-4

Upstream product

• 1379662-52-8 bicyclo[6.1.0]non-4-yn-9-ylmethanol 
• 7693-46-1 4-Nitrophenyl chloroformate 

Downstream Products

• 1613372-89-6 (2S,3S,4R)-1-O-(α-D-galactopyranosyl)-4-O-(hexacosanoyl)-2-(((N-(((bicyclo[6.1.0]non-4-yn-9-yl)methoxy)carbonyl)-Val-Cit-4-aminobenzyloxy)carbonyl)amino)octadecane-1,3,4-triol 
• 1951439-51-2 C₁₇H₂₇NO₅ 

Relevant academic research and scientific papers

Photo-induced and Rapid Labeling of Tetrazine-Bearing Proteins via Cyclopropenone-Caged Bicyclononynes

Inverse electron-demand Diels–Alder cycloadditions (iEDDAC) between tetrazines and strained alkenes/alkynes have emerged as essential tools for studying and manipulating biomolecules. A light-triggered version of iEDDAC (photo-iEDDAC) is presented that confers spatio-temporal control to bioorthogonal labeling in vitro and in cellulo. A cyclopropenone-caged dibenzoannulated bicyclo[6.1.0]nonyne probe (photo-DMBO) was designed that is unreactive towards tetrazines before light-activation, but engages in iEDDAC after irradiation at 365 nm. Aminoacyl tRNA synthetase/tRNA pairs were discovered for efficient site-specific incorporation of tetrazine-containing amino acids into proteins in living cells. In situ light activation of photo-DMBO conjugates allows labeling of tetrazine-modified proteins in living E. coli. This allows proteins in living cells to be modified in a spatio-temporally controlled manner and may be extended to photo-induced and site-specific protein labeling in animals.