ncAA Structure (png, jpg, jpeg)
ncAA Foundational Publication Support
Eddins, Alex J, Riley M Bednar, Subhashis Jana, Abigail H Pung, Lea Mbengi, Kyle Meyer, John J Perona, Richard B Cooley, Andrew Karplus, and Ryan A Mehl. (2023) 2023. “Truncation-Free Genetic Code Expansion With Tetrazine Amino Acids For Quantitative Protein Ligations.”. Bioconjugate Chemistry 34 (12): 2243-2254. doi:10.1021/acs.bioconjchem.3c00380.
ncAA Utility
An amino acid that contains a 1,2,4,5-tetrazine-ethyl group that can be used for bioorthogonal, click-chemistry reactions (bioconjugation) when reacted with trans-cyclooctenes (TCOs) which can themselves be bound to various moieties such as PEG linkers, fluorophores, spin labels, etc.. These click reactions require no catalysts and can be carried out either in vivo or in vitro. Also, when reacted with strained TCOs (sTCOs), the reaction rates are extremely fast, achieving second order rate constants in excess of 10,000 per molar per second.
ncAA Source
Exogenous - Synthesized
ncAA Availability
Tet2-Et can be purchased at the GCE4All site, here:
https://gce4all.oregonstate.edu/tetrazine-amino-acids
https://gce4all.oregonstate.edu/tetrazine-amino-acids
RS/tRNA Pair Usage Information
Upon the discovery that the Mj Tet2-D12RS that was selected for Tet2-Me worked even better with Tet2-Et, it was decided to switch from Tet2-Me to Tet2-Et for developing an E. coli GCE system that could generate high efficiency high fidelity expression in BL21 and B95 E. coli strains. The original RS was not satisfactory, and a better RS (the Tet2-Et E7RS) was selected for using Tet2-Et, and is now the RS of choice for high fidelity incorporation in BL21 cells, and truncation-free expression in the RF1-deficient B95 cells.
ncAA Synonyms
Tet2.0-Et
Tet2-ethyl
(S)-2-amino-3-(4-(6-ethyl-1,2,4,5-tetrazin-3-yl)phenyl) propanoic acid
tetrazine 2.0-ethyl
tetrazine 2-ethyl
Tet2-ethyl
(S)-2-amino-3-(4-(6-ethyl-1,2,4,5-tetrazin-3-yl)phenyl) propanoic acid
tetrazine 2.0-ethyl
tetrazine 2-ethyl
ChEBI ID
229636
PubChem Link