ncAA Structure (png, jpg, jpeg)
ncAA Foundational Publication Support
Park, Hee-Sung, Michael J Hohn, Takuya Umehara, Li-Tao Guo, Edith M Osborne, Jack Benner, Christopher J Noren, Jesse Rinehart, and Dieter Söll. (2011) 2011. “Expanding The Genetic Code Of Escherichia Coli With Phosphoserine.”. Science (New York, N.y.) 333 (6046): 1151-4. doi:10.1126/science.1207203.
Lee, Sangsik, Seunghee Oh, Aerin Yang, Jihyo Kim, Dieter Söll, Daeyoup Lee, and Hee-Sung Park. 2013. “A Facile Strategy For Selective Incorporation Of Phosphoserine Into Histones”. Angewandte Chemie International Edition 52: 5771-5775. doi:10.1002/anie.201300531.
Pirman, Natasha L., Karl W. Barber, Hans R. Aerni, Natalie J. Ma, Adrian D. Haimovich, Svetlana Rogulina, Farren J. Isaacs, and Jesse Rinehart. (sep) 2015. “A Flexible Codon In Genomically Recoded Escherichia Coli Permits Programmable Protein Phosphorylation”. Nature Communications 6: 8130. doi:10.1038/ncomms9130.
Rogerson, D. T., A. Sachdeva, K. Wang, T. Haq, A. Kazlauskaite, S. M. Hancock, N. Huguenin-Dezot, M. M. K. Muqit, A. M. Fry, and R. Bayliss. n.d. “Efficient Genetic Encoding Of Phosphoserine And Its Nonhydrolyzable Analog” 11: 496+.
Zhu, Phillip, Philip R Gafken, Ryan A Mehl, and Richard B Cooley. (2019) 2019. “A Highly Versatile Expression System For The Production Of Multiply Phosphorylated Proteins.”. Acs Chemical Biology 14 (7): 1564-1572. doi:10.1021/acschembio.9b00307.
Vesely, Cat Hoang, Patrick N Reardon, Zhen Yu, Elisar Barbar, Ryan A Mehl, and Richard B Cooley. (2022) 2022. “Accessing Isotopically Labeled Proteins Containing Genetically Encoded Phosphoserine For Nmr With Optimized Expression Conditions.”. The Journal Of Biological Chemistry 298 (12): 102613. doi:10.1016/j.jbc.2022.102613.
ncAA Protocols
Zhu, Phillip, Ryan A Mehl, and Richard B Cooley. (2022) 2022. “Site-Specific Incorporation Of Phosphoserine Into Recombinant Proteins In .”. Bio-Protocol 12 (21). doi:10.21769/BioProtoc.4541.
Barber, Karl, and Jesse Rinehart. (2017) 2017. “Expression Of Recombinant Phosphoproteins For Signal Transduction Studies.”. Methods In Molecular Biology (Clifton, N.j.) 1636: 71-78. doi:10.1007/978-1-4939-7154-1_5.
ncAA Usage Publications
Stuber, Katrin, Tobias Schneider, Jill Werner, Michael Kovermann, Andreas Marx, and Martin Scheffner. (2021) 2021. “Structural And Functional Consequences Of Nedd8 Phosphorylation.”. Nature Communications 12 (1): 5939. doi:10.1038/s41467-021-26189-9.
Vesely, Cat Hoang, Patrick N Reardon, Zhen Yu, Elisar Barbar, Ryan A Mehl, and Richard B Cooley. (2022) 2022. “Accessing Isotopically Labeled Proteins Containing Genetically Encoded Phosphoserine For Nmr With Optimized Expression Conditions.”. The Journal Of Biological Chemistry 298 (12): 102613. doi:10.1016/j.jbc.2022.102613.
ncAA Utility
Used to produce proteins site-specifically phosphorylated at serine residues, typically at positions where phosphoserine naturally occurs as a post-translational modification
ncAA Source
Endogenous
ncAA Availability
pSer is the natural precursor to serine, and by knocking out the SerB enzyme (catalyzing last step in Ser production pathway), intracellular pSer builds up. The relevant RS/tRNA entries give information on ΔserB cell lines used.
Also available from https://www.sigmaaldrich.com/US/en/product/sigma/p0878
Also available from https://www.sigmaaldrich.com/US/en/product/sigma/p0878
RS/tRNA Pair Usage Information
In terms of both expression efficiency and fidelity in E. coli and mammalian cells, earlier pSer incorporation systems are superceded by the SepRS2 system. The SepRS9 system is still in used in a system that uses E. coli to produce a library of peptides representing the human pSer proteome to look at protein-protein interactions using the Hi-P system.
ncAA Synonyms
(2S)-2-amino-3-(phosphonooxy)propanoic acid
O-phosphoserine
pSer
O-phospho-L-serine
O-phosphono-L-serine
dl-O-Phosphoserine
O-Phospho-L-serine
DL-Serine dihydrogen phosphate
Serophen
Energoserina
serine, O-phosphono-
P-serine
o-Phosphonoserine
2-amino-3-phosphonooxypropanoic acid
DL-O-Phosphorylserine
DL-Serine monophosphoric acid
phosphorylserine
DL-Phosphoserine
3-phospho-serine
O-phosphoserine
pSer
O-phospho-L-serine
O-phosphono-L-serine
dl-O-Phosphoserine
O-Phospho-L-serine
DL-Serine dihydrogen phosphate
Serophen
Energoserina
serine, O-phosphono-
P-serine
o-Phosphonoserine
2-amino-3-phosphonooxypropanoic acid
DL-O-Phosphorylserine
DL-Serine monophosphoric acid
phosphorylserine
DL-Phosphoserine
3-phospho-serine
ChEBI ID
15811
PubChem Link
PDB Code
SEP