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3-nitro-L-phenylalanine

3-nitro-L-phenylalanine

ncAA Foundational Publication Support

Wang, Yane-Shih, Xinqiang Fang, Hsueh-Ying Chen, Bo Wu, Zhiyong U Wang, Christian Hilty, and Wenshe R Liu. (2013) 2013. “Genetic Incorporation Of Twelve Meta-Substituted Phenylalanine Derivatives Using A Single Pyrrolysyl-Trna Synthetase Mutant.”. Acs Chemical Biology 8 (2): 405-15. doi:10.1021/cb300512r.
Porter, Joseph J, Hyo Sang Jang, Elise M Van Fossen, Duy P Nguyen, Taylor S Willi, Richard B Cooley, and Ryan A Mehl. (2019) 2019. “Genetically Encoded Protein Tyrosine Nitration In Mammalian Cells.”. Acs Chemical Biology 14 (6): 1328-1336. doi:10.1021/acschembio.9b00371.
ncAA Utility
can quench Trp fluoresence via FRET in a distance dependent manner. May also be useful as a control for use in studies of the roles of 3-nitroTyr in protein structure-function.
ncAA Source
Exogenous - Purchased
ncAA Availability
Can be purchased https://www.thermofisher.com/order/catalog/product/H63029.06
RS/tRNA Pair Usage Information
The N346A/C348A RS incorporated at medium levels into sfGFP2TAG (10 mg/L) with high fidelity in E coli grown with 2 mM ncAA in GMML media. No direct comparison is available for these RS, but the very high (~750 mg/L) sfGFP(150) production in E coli by the F4 RS may be evidence of a greater efficiency. The 2019 foundational paper also documented that the F4 RS led to ~25% efficiency expression of 3-nitroPhe containing sfGFP(150) in HEK293T cells.

RS/tRNA Pair(s)

ncAA Synonyms
19883-74-0
(S)-2-amino-3-(3-nitrophenyl)propanoic acid
3-Nitro-L-phenylalanine
L-3-NITROPHENYLALANINE
L-Phenylalanine, 3-nitro-
(2S)-2-amino-3-(3-nitrophenyl)propanoic acid
NSC-21948
L-3-Nitrophe
MFCD01860661
3-nitrophenylalanine
ChEBI ID
233129
ChEBI Link
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI%3A233129&conversationCont…
PubChem Link
https://pubchem.ncbi.nlm.nih.gov/compound/2761812
ncAA Additional Notes
was shown by 2019 foundational paper to not be toxic in HEK293T cells at a 1 mM concentration.