Norbornene-methoxycarbonyl-Lysine | GCE4All Knowledge Base

ncAA Foundational Publication Support

Plass, Tilman, Sigrid Milles, Christine Koehler, Jędrzej Szymański, Rainer Mueller, Manfred Wiessler, Carsten Schultz, and Edward A Lemke. (2012) 2012. “Amino Acids For Diels-Alder Reactions In Living Cells.”. Angewandte Chemie (International Ed. In English) 51 (17): 4166-70. doi:10.1002/anie.201108231.

Kaya, Emine, Milan Vrabel, Christian Deiml, Stefan Prill, Viviana Fluxa, and Thomas Carell. (2012) 2012. “A Genetically Encoded Norbornene Amino Acid For The Mild And Selective Modification Of Proteins In A Copper-Free Click Reaction.”. Angewandte Chemie (International Ed. In English) 51 (18): 4466-9. doi:10.1002/anie.201109252.

Vrabel, Milan, Patrick Kölle, Korbinian Brunner, Michael J Gattner, Verónica López-Carrillo, Regina de Vivie-Riedle, and Thomas Carell. (2013) 2013. “Norbornenes In Inverse Electron-Demand Diels-Alder Reactions.”. Chemistry (Weinheim An Der Bergstrasse, Germany) 19 (40): 13309-12. doi:10.1002/chem.201301838.

ncAA Usage Publications

Scheidler, Christopher M, Milan Vrabel, and Sabine Schneider. (2020) 2020. “Genetic Code Expansion, Protein Expression, And Protein Functionalization In .”. Acs Synthetic Biology 9 (3): 486-493. doi:10.1021/acssynbio.9b00458.

Schneider, Sabine, Michael J Gattner, Milan Vrabel, Veronika Flügel, Verónica López-Carrillo, Stefan Prill, and Thomas Carell. (2013) 2013. “Structural Insights Into Incorporation Of Norbornene Amino Acids For Click Modification Of Proteins.”. Chembiochem : A European Journal Of Chemical Biology 14 (16): 2114-8. doi:10.1002/cbic.201300435.

ncAA Utility

Useful for click-chemistry with nitrile imines and tetrazines

ncAA Source

Exogenous - Purchased

ncAA Availability

https://www.medchemexpress.com/h-l-lys-norbornene-methoxycarbonyl-oh.html

RS/tRNA Pair Usage Information

The MmRS-AF mutant yielded ~10 mg/L GFP with the ncAA at residue 4 and also incorporated well in a test protein in Hela cells with maximal incorporation occurring at about 100 microM.

norb-PylRS produced a polymerase kappa at 2 mg/l, and was also shown to work in B subtilis cells to produce ncAA-GFP(26) at ~20 mg/L. shown in structural insights" paper that can put in both endo- and exo-isomers similarly (9 mg/L into carbonic anhydrase).

it is not clear how the two RSs compare in efficiency and fidelity.