ncAA Structure (png, jpg, jpeg)
ncAA Foundational Publication Support
Tharp, Jeffery M, Yane-Shih Wang, Yan-Jiun Lee, Yanyan Yang, and Wenshe R Liu. (2014) 2014. “Genetic Incorporation Of Seven Ortho-Substituted Phenylalanine Derivatives.”. Acs Chemical Biology 9 (4): 884-90. doi:10.1021/cb400917a.
ncAA Usage Publications
Tharp, Jeffery M, Yane-Shih Wang, Yan-Jiun Lee, Yanyan Yang, and Wenshe R Liu. (2014) 2014. “Genetic Incorporation Of Seven Ortho-Substituted Phenylalanine Derivatives.”. Acs Chemical Biology 9 (4): 884-90. doi:10.1021/cb400917a.
ncAA Utility
Potentially useful as fluorescence-based environmental sensor to study protein conformation. Also, can be an IR probe.
ncAA Source
Exogenous - Purchased
ncAA Availability
can be purchased from https://www.sigmaaldrich.com/US/en/product/achemblock/advh14dbaf5f?context=bbe
RS/tRNA Pair Usage Information
Yielded 35 mg/L GFPTAG2 when at 2 mM in E. coli using GMML media. Fidelity confirmed by MS. In LB media yielded 56 mg/L (~3 times that obtained with Phe) of GFPTAG27. No MS done. Also put into GFPTAG135 and (in TOP10 E. coli cells) MPPTAG8 to show fluorescence depends on environment and can monitor unfolding. Yielded 4.9 fold increase in fluorescence using HEK293T cells to produce an EGFR-GFPTAG128 when at 5 mM. No MS done.
ncAA Synonyms
263396-42-5
L-2-Cyanophenylalanine
2-Cyano-L-Phenylalanine
H-Phe(2-CN)-OH
(S)-2-Amino-3-(2-cyanophenyl)propanoic acid
L-2-Cyanophe
(2S)-2-amino-3-(2-cyanophenyl)propanoic acid
L-2-Cyanophenylalarine
L-Phenylalanine, 2-cyano-
DTXSID80375804
L-2-Cyanophenylalanine
2-Cyano-L-Phenylalanine
H-Phe(2-CN)-OH
(S)-2-Amino-3-(2-cyanophenyl)propanoic acid
L-2-Cyanophe
(2S)-2-amino-3-(2-cyanophenyl)propanoic acid
L-2-Cyanophenylalarine
L-Phenylalanine, 2-cyano-
DTXSID80375804
ChEBI ID
233128
PubChem Link