ncAA Structure (png, jpg, jpeg)
ncAA Foundational Publication Support
Chin, Jason W., Stephen W. Santoro, Andrew B. Martin, David S. King, Lei Wang, and Peter G. Schultz. (aug) 2002. “Addition Of P-Azido-L-Phenylalanine To The Genetic Code Of Escherichia Coli”. Journal Of The American Chemical Society 124: 9026-9027. doi:10.1021/ja027007w.
Young, Douglas D, Travis S Young, Michael Jahnz, Insha Ahmad, Glen Spraggon, and Peter G Schultz. (2011) 2011. “An Evolved Aminoacyl-Trna Synthetase With Atypical Polysubstrate Specificity.”. Biochemistry 50 (11): 1894-900. doi:10.1021/bi101929e.
Seidel, Lisa, Barbara Zarzycka, Saheem Zaidi, Vsevolod Katritch, and Irene Coin. (2017) 2017. “Structural Insight Into The Activation Of A Class B G-Protein-Coupled Receptor By Peptide Hormones In Live Human Cells.”. Elife 6. doi:10.7554/eLife.27711.
ncAA Protocols
Lightle, Hailey E, Parmila Kafley, Todd R Lewis, and Rongsheng E Wang. (2023) 2023. “Site-Specific Protein Conjugates Incorporating Para-Azido-L-Phenylalanine For Cellular And In Vivo Imaging.”. Methods (San Diego, Calif.) 219: 95-101. doi:10.1016/j.ymeth.2023.10.001.
ncAA Utility
Used as a photocrosslinker, allowing for crosslinking and bioorthogonal ligation of protein.
ncAA Source
Exogenous - Purchased
ncAA Availability
Can be purchased from https://www.sigmaaldrich.com/US/en/product/sial/909564
RS/tRNA Pair Usage Information
This RS/tRNA pair was evolved with MAGE[ multiplex automated genome engineering]. The evolved pair has been shown to have a 25-fold higher expression of pAzF in GFP[3UAG] compared to the progenitor enzyme (pAcFRS). This pair has also been shown to be promiscuous, and specifically also incorporates pAcF.
For incorporation in mammalian cells, the EAziRS is available from Addgene and seems to be the go-to system.
For incorporation in mammalian cells, the EAziRS is available from Addgene and seems to be the go-to system.
RS/tRNA Pair(s)
ncAA Synonyms
4-Azido-L-phenylalanine
H-P-AZIDO-PHE-OH
4-Azidophenylalanine
(S)-2-Amino-3-(4-azidophenyl)propanoic acid
p-azidophenylalanine
p-azido-l-phenylalanine
(2S)-2-amino-3-(4-azidophenyl)propanoic acid
L-Phenylalanine, 4-azido-
AZF
pAzF
p-azido-L-Phe
H-P-AZIDO-PHE-OH
4-Azidophenylalanine
(S)-2-Amino-3-(4-azidophenyl)propanoic acid
p-azidophenylalanine
p-azido-l-phenylalanine
(2S)-2-amino-3-(4-azidophenyl)propanoic acid
L-Phenylalanine, 4-azido-
AZF
pAzF
p-azido-L-Phe
ChEBI ID
228211
ncAA Additional Notes
N/A