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4'-TCOK (TCO)

4'TCO-lysine

ncAA Foundational Publication Support

Lang, Kathrin, Lloyd Davis, Stephen Wallace, Mohan Mahesh, Daniel J Cox, Melissa L Blackman, Joseph M Fox, and Jason W Chin. (2012) 2012. ā€œGenetic Encoding of Bicyclononynes and Trans-Cyclooctenes for Site-Specific Protein Labeling in Vitro and in Live Mammalian Cells via Rapid Fluorogenic Diels-Alder Reactionsā€. Journal of the American Chemical Society 134 (25): 10317-20. doi:10.1021/ja302832g.
Peng, Tao, and Howard C Hang. (2016) 2016. ā€œSite-Specific Bioorthogonal Labeling for Fluorescence Imaging of Intracellular Proteins in Living Cellsā€. Journal of the American Chemical Society 138 (43): 14423-33.
ncAA Utility
Reactive handle for IEDDA.
ncAA Source
Exogenous - Purchased
ncAA Availability
SiChem catalog #SC8004 is the axial isomer, and #SC8060 is the equatorial isomer
RS/tRNA Pair Usage Information
Peng & Hang (2016) showed the UP50 values for the 4'-axial, and 4'-equitorial TCOK were roughly 800 and 200 microM respectively. They also showed that the MmPylRS-AF synthetase did not incorporate the 4'-TCOK ncAAs.

RS/tRNA Pair(s)

ncAA Synonyms
trans-cyclooct-4-ene-L-lysine
TCO
TCOK
TCO4/EQ
TCO4/AX
TCO4
ChEBI ID
233068
ChEBI Link
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI%3A233068&conversationContā€¦
ncAA Additional Notes
Peng & Hong (2016) noted the 2'-axial TCOK (a.k.a TCO* or TCO*A) is more stable than the 4' isomer