ncAA Structure (png, jpg, jpeg)
ncAA Foundational Publication Support
Lang, Kathrin, Lloyd Davis, Jessica Torres-Kolbus, Chungjung Chou, Alexander Deiters, and Jason W Chin. (2012) 2012. “Genetically Encoded Norbornene Directs Site-Specific Cellular Protein Labelling Via A Rapid Bioorthogonal Reaction.”. Nature Chemistry 4 (4): 298-304. doi:10.1038/nchem.1250.
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.
ncAA Protocols
Nikić, Ivana, Jun Hee Kang, Gemma Estrada Girona, Iker Valle Aramburu, and Edward A Lemke. (2015) 2015. “Labeling Proteins On Live Mammalian Cells Using Click Chemistry.”. Nature Protocols 10 (5): 780-91. doi:10.1038/nprot.2015.045.
ncAA Usage Publications
Lang, Kathrin, Lloyd Davis, Stephen Wallace, Mohan Mahesh, Daniel J Cox, Melissa L Blackman, Joseph M Fox, and Jason W Chin. (2012) 2012. “Genetic Encoding Of Bicyclononynes And Trans-Cyclooctenes For Site-Specific Protein Labeling In Vitro And In Live Mammalian Cells Via Rapid Fluorogenic Diels-Alder Reactions.”. Journal Of The American Chemical Society 134 (25): 10317-20. doi:10.1021/ja302832g.
ncAA Utility
Reactive handle for IEDDA
ncAA Source
Exogenous - Synthesized
ncAA Availability
SciChem catalog #SC8005
RS/tRNA Pair Usage Information
Both RSs were published in the same year. Plass et al reported that the MmRS-AF mutant yielded ~10 mg/L GFP with the ncAA at residue 4 (and MmRS-WT could put it in somewhat less well), and Lang et al reported that the WT MbRS yielded ~4 mg/L GFP with ncAA at residue 150. Also was shown to work in mammalian cell systems.
ncAA Synonyms
Nε-5-Norbornene-2-yloxycarbonyl-L-lysine
(S)-2-Amino-6-((((1R,4R)-bicyclo[2.2.1]hept-5-en-2-yloxy)carbonyl)amino)hexanoic acid
Norbornene-O–L-Lysine (NBO)
(S)-2-Amino-6-((((1R,4R)-bicyclo[2.2.1]hept-5-en-2-yloxy)carbonyl)amino)hexanoic acid
Norbornene-O–L-Lysine (NBO)
ChEBI ID
233110
PubChem Link
ncAA Additional Notes
Has been successfully used in mammalian cells, but reported by Plass et al (2012) to not react as fast as TCOs or strained alkynes.