Azidonorleucine

ncAA Structure (png, jpg, jpeg)
azidonorleucine

ncAA Foundational Publication Support

Link, James, Mandy Vink, Nicholas Agard, Jennifer A Prescher, Carolyn R Bertozzi, and David A Tirrell. (2006) 2006. “Discovery Of Aminoacyl-Trna Synthetase Activity Through Cell-Surface Display Of Noncanonical Amino Acids.”. Proceedings Of The National Academy Of Sciences Of The United States Of America 103 (27): 10180-10185. doi:10.1073/pnas.0601167103.

Tanrikulu, Caglar, Emmanuelle Schmitt, Yves Mechulam, William A Goddard, and David A Tirrell. (2009) 2009. “Discovery Of Escherichia Coli Methionyl-Trna Synthetase Mutants For Efficient Labeling Of Proteins With Azidonorleucine In Vivo.”. Proceedings Of The National Academy Of Sciences Of The United States Of America 106 (36): 15285-90. doi:10.1073/pnas.0905735106.

Erdmann, Ines, Kathrin Marter, Oliver Kobler, Sven Niehues, Julia Abele, Anke Müller, Julia Bussmann, et al. (2015) 2015. “Cell-Selective Labelling Of Proteomes In Drosophila Melanogaster.”. Nature Communications 6: 7521. doi:10.1038/ncomms8521.

Mahdavi, Alborz, Graham D Hamblin, Granton A Jindal, John D Bagert, Cathy Dong, Michael J Sweredoski, Sonja Hess, Erin M Schuman, and David A Tirrell. (2016) 2016. “Engineered Aminoacyl-Trna Synthetase For Cell-Selective Analysis Of Mammalian Protein Synthesis.”. Journal Of The American Chemical Society 138 (13): 4278-81. doi:10.1021/jacs.5b08980.

ncAA Usage Publications

Ngo, John T, Julie Champion, Alborz Mahdavi, Caglar Tanrikulu, Kimberly Beatty, Rebecca Connor, Tae Hyeon Yoo, Daniela C Dieterich, Erin M Schuman, and David A Tirrell. (2009) 2009. “Cell-Selective Metabolic Labeling Of Proteins.”. Nature Chemical Biology 5 (10): 715-7. doi:10.1038/nchembio.200.

Ngo, John T, Erin M Schuman, and David A Tirrell. (2013) 2013. “Mutant Methionyl-Trna Synthetase From Bacteria Enables Site-Selective N-Terminal Labeling Of Proteins Expressed In Mammalian Cells.”. Proceedings Of The National Academy Of Sciences Of The United States Of America 110 (13): 4992-7. doi:10.1073/pnas.1216375110.

Mahdavi, Alborz, Janek Szychowski, John T Ngo, Michael J Sweredoski, Robert L J Graham, Sonja Hess, Olaf Schneewind, Sarkis K Mazmanian, and David A Tirrell. (2014) 2014. “Identification Of Secreted Bacterial Proteins By Noncanonical Amino Acid Tagging.”. Proceedings Of The National Academy Of Sciences Of The United States Of America 111 (1): 433-8. doi:10.1073/pnas.1301740111.

ncAA Utility
Biorthogonal Ligation, Click Chemistry labeling with fluorescence or affinity labels. Specifically used for cell-specific proteomics studies using "bioorthogonal noncanonical amino acid tagging" (BONCAT) proteomics. Contrasts with Azidohomoalanine which does not allow cell-specific studies.
ncAA Source
Exogenous - Purchased
ncAA Availability
can be purchased from https://www.tocris.com/products/l-azidonorleucine-hydrochloride_6585

RS/tRNA Pair Usage Information
For use in E. coli, the NLL MetRS supercedes the MetRS-L13G.
The NLL MetRS can also be used in mammalian cells (and a stable HEK cell line has been made), but only puts Anl into initiator methionine positions.

The drosophila-based MetRS-L262G and the mouse-based L274G MmMetRS both work in live drosophila with MetRS-L262G somewhat better tolerated, and the murine based L274G MmMetRS works well in multiple mammalian cell lines.

RS/tRNA Pair(s)


ncAA Synonyms
azidonorleucine
6-Azido-L-Norleucine
(2S)-2-amino-6-azidohexanoic acid
159610-92-1
L-Azidonorleucine
H-Lys(N3)
ChEBI ID
233439