ncAA Structure (png, jpg, jpeg)
ncAA Foundational Publication Support
Chin, Jason W., Andrew B. Martin, David S. King, Lei Wang, and Peter G. Schultz. (aug) 2002. “Addition Of A Photocrosslinking Amino Acid To The Genetic Code Of Escherichia Coli”. Proceedings Of The National Academy Of Sciences 99: 11020-11024. doi:10.1073/pnas.172226299.
Stokes, Audrey L, Shigeki J Miyake-Stoner, Jennifer C Peeler, Duy P Nguyen, Robert P Hammer, and Ryan A Mehl. (2009) 2009. “Enhancing The Utility Of Unnatural Amino Acid Synthetases By Manipulating Broad Substrate Specificity.”. Molecular Biosystems 5 (9): 1032-8. doi:10.1039/b904032c.
ncAA Protocols
Peeler, Jennifer C, and Ryan A Mehl. (2012) 2012. “Site-Specific Incorporation Of Unnatural Amino Acids As Probes For Protein Conformational Changes.”. Methods In Molecular Biology (Clifton, N.j.) 794: 125-34. doi:10.1007/978-1-61779-331-8_8.
Cooley, Richard B, and Holger Sondermann. (2017) 2017. “Probing Protein-Protein Interactions With Genetically Encoded Photoactivatable Cross-Linkers.”. Methods In Molecular Biology (Clifton, N.j.) 1657: 331-345. doi:10.1007/978-1-4939-7240-1_26.
ncAA Usage Publications
Nelson, Brock, Nathan Soper, and Tania J. Lupoli. (oct) 2023. “Bacterial J-Domains With C-Terminal Tags Contact The Substrate Binding Domain Of Dnak And Sequester Chaperone Activity”. Chembiochem: A European Journal Of Chemical Biology 24: e202300261. doi:10.1002/cbic.202300261.
Tholen, Marrit M. E., Bas J. H. M. Rosier, Robin T. Vermathen, Céline A. N. Sewnath, Cornelis Storm, Laura Woythe, Cristina Izquierdo-Lozano, et al. (jun) 2023. “Mapping Antibody Domain Exposure On Nanoparticle Surfaces Using Dna-Paint”. Acs Nano 17: 11665-11678. doi:10.1021/acsnano.3c02195.
Blueggel, Mike, Alexander Kroening, Matthias Kracht, Johannes van den Boom, Matthias Dabisch, Anna Goehring, Farnusch Kaschani, et al. (jun) 2023. “The Ubx Domain In Ubxd1 Organizes Ubiquitin Binding At The C-Terminus Of The Vcp/P97 Aaa-Atpase”. Nature Communications 14: 3258. doi:10.1038/s41467-023-38604-4.
van den Boom, Johannes, Guendalina Marini, Hemmo Meyer, and Helen R. Saibil. (jul) 2023. “Structural Basis Of Ubiquitin-Independent Pp1 Complex Disassembly By P97”. The Embo Journal 42: e113110. doi:10.15252/embj.2022113110.
van Aalen, Eva A., Bas J. H. M. Rosier, Tom Jansen, Simone F. A. Wouters, Robin T. Vermathen, Harmen J. van der Veer, José Yeste Lozano, et al. (jun) 2023. “Integrated Bioluminescent Immunoassays For High-Throughput Sampling And Continuous Monitoring Of Cytokines”. Analytical Chemistry 95: 8922-8931. doi:10.1021/acs.analchem.3c00745.
Sato, Shin, Shinya Mimasu, Aya Sato, Nobumasa Hino, Kensaku Sakamoto, Takashi Umehara, and Shigeyuki Yokoyama. (2011) 2011. “Crystallographic Study Of A Site-Specifically Cross-Linked Protein Complex With A Genetically Incorporated Photoreactive Amino Acid.”. Biochemistry 50 (2): 250-7.
ncAA Utility
Used as a photocrosslinker, allowing for crosslinking and bioorthogonal ligation of protein.
ncAA Source
Exogenous - Purchased
ncAA Availability
Commercially available from mulitple sources including Fisher Scientific as product AAH52083MD and from Bachem as Product Number: 4017646
RS/tRNA Pair Usage Information
A head-to-head comparison of the two RSs reported in foundational paper 2 indicates that the BpaRS-T158S,A31V gives over twice the yield of the original BpaRS. However the original one appears to be the one generally used and it is available from Addgene.
ncAA Synonyms
Bpa
p-Bpa
L-4-Benzoylphenylalanine
4-benzoyl-l-phenylalanine
(S)-2-Amino-3-(4-benzoylphenyl)propanoic acid
Para-(Benzoyl)-Phenylalanine
p-benzoyl-l-phenylalanine
4-benzoylphenylalanine
L-Phenylalanine, 4-benzoyl-
L-p-Benzoylphenylalanine
p-Bpa
L-4-Benzoylphenylalanine
4-benzoyl-l-phenylalanine
(S)-2-Amino-3-(4-benzoylphenyl)propanoic acid
Para-(Benzoyl)-Phenylalanine
p-benzoyl-l-phenylalanine
4-benzoylphenylalanine
L-Phenylalanine, 4-benzoyl-
L-p-Benzoylphenylalanine
ChEBI ID
44718
ncAA Additional Notes
N/A