Fosfoserina

L-Fosfoserina
	Fórmula esquelética
	Modelo de bólas e barras
	Nome IUPAC Ácido (S)-2-amino-3-(fosfonooxi)propiónico
Identificadores
Número CAS	407-41-0
PubChem	106
ChemSpider	62074
UNII	VI4F0K069V
DrugBank	DB04522
KEGG	C01005
MeSH	Phosphoserine
ChEBI	CHEBI:15811
ChEMBL	CHEMBL284377
Ligando IUPHAR	1411
Imaxes 3D Jmol	Image 1
	SMILES O=P(O)(O)OC[C@@H](C(=O)O)N ;
	InChI InChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)/t2-/m0/s1; Key: BZQFBWGGLXLEPQ-REOHCLBHSA-N InChI=1/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)/t2-/m0/s1;
Propiedades
Fórmula molecular	C3H8NO6P
Masa molecular	185,073 g/mol
Punto de fusión	228 °C; 442 °F; 501 K
	; Se non se indica outra cousa, os datos están tomados en condicións estándar de 25 °C e 100 kPa.

A fosfoserina (abreviada como SEP ou J) é un éster do aminoácido serina e un ácido fosfórico. A fosfoserina é un compoñente de moitas proteínas como resultado da súa modificación postraducional.^[1] A fosforilación do grupo funcional alcohol da serina para producir fosfoserina é catalizada por varios tipos de quinases.^[2]^[3] Ningún codón do código xenético codifica de forma natural a fosfoserina, polo que non se introduce nas proteínas durante a súa tradución. Porén, utilizando tecnoloxías que fan uso dun código xenético expandido, a fosfoserina pode tamén incorporarse ás proteínas durante a tradución.^[4]^[5]^[6]

É un metabolito normal que se encontra en biofluídos humanos.^[7]

A fosfoserina ten tres sitios de coordinación potenciais (grupos carboxilo, amino e fosfato) A determinación do modo de coordinación entre ligandos fosforilados e ións metálicos que ocorre nun organismo é un primeiro paso para explicar a función da fosfoserina nos procesos bioinorgánicos.^[8]^[9]

Notas

↑ Olsen, Jesper V.; Blagoev, Blagoy; Gnad, Florian; Macek, Boris; Kumar, Chanchal; Mortensen, Peter; Mann, Matthias (2006-03-11). "Global, In Vivo, and Site-Specific Phosphorylation Dynamics in Signaling Networks". Cell 127 (3): 635–648. PMID 17081983. doi:10.1016/j.cell.2006.09.026.
↑ Krebs, Edwin G. (1985-10-01). "The phosphorylation of proteins: a major mechanism for biological regulation". Biochemical Society Transactions 13 (5): 813–820. PMID 2998902. doi:10.1042/bst0130813.
↑ Manning, G.; Whyte, D. B.; Martinez, R.; Hunter, T.; Sudarsanam, S. (2002-12-06). "The Protein Kinase Complement of the Human Genome". Science 298 (5600): 1912–1934. Bibcode:2002Sci...298.1912M. PMID 12471243. doi:10.1126/science.1075762.
↑ Park, Hee-Sung; Hohn, Michael J.; Umehara, Takuya; Guo, Li-Tao; Osborne, Edith M.; Benner, Jack; Noren, Christopher J.; Rinehart, Jesse; Söll, Dieter (2011-08-26). "Expanding the Genetic Code of Escherichia coli with Phosphoserine". Science 333 (6046): 1151–1154. Bibcode:2011Sci...333.1151P. PMC 5547737. PMID 21868676. doi:10.1126/science.1207203.
↑ Rogerson, Daniel T; Sachdeva, Amit; Wang, Kaihang; Haq, Tamanna; Kazlauskaite, Agne; Hancock, Susan M; Huguenin-Dezot, Nicolas; Muqit, Miratul M K; Fry, Andrew M (2015-01-01). "Efficient genetic encoding of phosphoserine and its nonhydrolyzable analog". Nature Chemical Biology 11 (7): 496–503. PMC 4830402. PMID 26030730. doi:10.1038/nchembio.1823.
↑ Oza, Javin P.; Aerni, Hans R.; Pirman, Natasha L.; Barber, Karl W.; ter Haar, Charlotte M.; Rogulina, Svetlana; Amrofell, Matthew B.; Isaacs, Farren J.; Rinehart, Jesse (2015-09-09). "Robust production of recombinant phosphoproteins using cell-free protein synthesis". Nature Communications 6: 8168. Bibcode:2015NatCo...6.8168O. PMC 4566161. PMID 26350765. doi:10.1038/ncomms9168.
↑ Kataoka, H; Nakai, K; Katagiri, Y; Makita, M (1993). "Analysis of free and bound O-phosphoamino acids in urine by gas chromatography with flame photometric detection". Biomedical Chromatography 7 (4): 184–8. PMID 7693088. doi:10.1002/bmc.1130070403.
↑ Jastrzab, Renata; Lomozik, Lechoslaw (2009-03-10). "Coordination mode in the binary systems of copper(II)/O-phospho-L-serine". Journal of Coordination Chemistry 62 (5): 710–720. doi:10.1080/00958970802317855.
↑ Jastrzab, Renata (2009-05-01). "Phosphoserine and specific types of its coordination in copper(II) and adenosine nucleotides systems – Potentiometric and spectroscopic studies". Journal of Inorganic Biochemistry 103 (5): 766–773. PMID 19230980. doi:10.1016/j.jinorgbio.2009.01.012.

[1] Olsen, Jesper V.; Blagoev, Blagoy; Gnad, Florian; Macek, Boris; Kumar, Chanchal; Mortensen, Peter; Mann, Matthias (2006-03-11). "Global, In Vivo, and Site-Specific Phosphorylation Dynamics in Signaling Networks". Cell 127 (3): 635–648. PMID 17081983. doi:10.1016/j.cell.2006.09.026.

[2] Krebs, Edwin G. (1985-10-01). "The phosphorylation of proteins: a major mechanism for biological regulation". Biochemical Society Transactions 13 (5): 813–820. PMID 2998902. doi:10.1042/bst0130813.

[3] Manning, G.; Whyte, D. B.; Martinez, R.; Hunter, T.; Sudarsanam, S. (2002-12-06). "The Protein Kinase Complement of the Human Genome". Science 298 (5600): 1912–1934. Bibcode:2002Sci...298.1912M. PMID 12471243. doi:10.1126/science.1075762.

[4] Park, Hee-Sung; Hohn, Michael J.; Umehara, Takuya; Guo, Li-Tao; Osborne, Edith M.; Benner, Jack; Noren, Christopher J.; Rinehart, Jesse; Söll, Dieter (2011-08-26). "Expanding the Genetic Code of Escherichia coli with Phosphoserine". Science 333 (6046): 1151–1154. Bibcode:2011Sci...333.1151P. PMC 5547737. PMID 21868676. doi:10.1126/science.1207203.

[5] Rogerson, Daniel T; Sachdeva, Amit; Wang, Kaihang; Haq, Tamanna; Kazlauskaite, Agne; Hancock, Susan M; Huguenin-Dezot, Nicolas; Muqit, Miratul M K; Fry, Andrew M (2015-01-01). "Efficient genetic encoding of phosphoserine and its nonhydrolyzable analog". Nature Chemical Biology 11 (7): 496–503. PMC 4830402. PMID 26030730. doi:10.1038/nchembio.1823.

[6] Oza, Javin P.; Aerni, Hans R.; Pirman, Natasha L.; Barber, Karl W.; ter Haar, Charlotte M.; Rogulina, Svetlana; Amrofell, Matthew B.; Isaacs, Farren J.; Rinehart, Jesse (2015-09-09). "Robust production of recombinant phosphoproteins using cell-free protein synthesis". Nature Communications 6: 8168. Bibcode:2015NatCo...6.8168O. PMC 4566161. PMID 26350765. doi:10.1038/ncomms9168.

[7] Kataoka, H; Nakai, K; Katagiri, Y; Makita, M (1993). "Analysis of free and bound O-phosphoamino acids in urine by gas chromatography with flame photometric detection". Biomedical Chromatography 7 (4): 184–8. PMID 7693088. doi:10.1002/bmc.1130070403.

[8] Jastrzab, Renata; Lomozik, Lechoslaw (2009-03-10). "Coordination mode in the binary systems of copper(II)/O-phospho-L-serine". Journal of Coordination Chemistry 62 (5): 710–720. doi:10.1080/00958970802317855.

[9] Jastrzab, Renata (2009-05-01). "Phosphoserine and specific types of its coordination in copper(II) and adenosine nucleotides systems – Potentiometric and spectroscopic studies". Journal of Inorganic Biochemistry 103 (5): 766–773. PMID 19230980. doi:10.1016/j.jinorgbio.2009.01.012.

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