407-41-0

O-Phospho-L-Serine is an agonist of the group III metabotropic glutamate receptors mGluR4a and mGluR6 (EC₅₀s = 2-5 μM). It mimics the phosphatidylserine head group and has been shown to inhibit the proliferation of microglia and to enhance neuronal differentiation of progenitor cells.

White powder

L-O-Phosphoserine is the catalytic domain of human protein kinase C β II when complexed with a malemide inhibitor. It is also used in the purification of the Epstein-Barr virus nuclear antigen 2A.

O-Phospho-L-Serine is an agonist of the group III metabotropic glutamate receptors mGluR4a and mGluR6 (EC50s = 2-5 μM). It mimics the phosphatidylserine head group and has been shown to inhibit the proliferation of microglia and to enhance neuronal differentiation of progenitor cells.

roborant

ChEBI:O-phospho-L-serine is the L-enantiomer of O-phosphoserine. It has a role as an EC 1.4.7.1 [glutamate synthase (ferredoxin)] inhibitor, a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, an EC 2.5.1.49 (O-acetylhomoserine aminocarboxypropyltransferase) inhibitor, an EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor and a mouse metabolite. It is a conjugate acid of an O-phosphonato-L-serine(2-). It is an enantiomer of an O-phospho-D-serine.

Notclassified

Group III metabotropic glutamate receptor agonist; analog of L-AP4 (L-(+)-2-Amino-4-phosphonobutyric acid ). Inhibits proliferation and enhances neuronal differentiation in progenitor cells.

Protein phosphorylation and dephosphorylation are basic signaling mechanisms that modify protein function in eukaryotic cells. Phosphorylation is a rare posttranslational event in normal tissues, however, the abundance of phosphorylated cellular proteins increases several folds following various activation processes. The main amino acids that are phosphorylated are tyrosine, serine, or threonine (pTyr/pSer/pThr), each having specific kinases that phosphorylate them and specific phosphatases that dephosphorylate them. Mono and polyclonal antibodies directed against phosphorylated residues were generated and found useful as analytical and preparative tools by enabling the identification, quantification, and immunoaffinity isolation of phosphorylated cellular proteins.

Store at -20°C

Recrystallise the phospho-serine by dissolving 10g in H2O (150mL) at 25o, stirring for up to 20minutes. Undissolved material is filtered off (Büchner), and 95% EtOH (85mL) is added dropwise during 4minutes, and set aside at 25o for 3hours, then at 3o overnight. The crystals are washed with 95% EtOH (100mL), then dry Et2O (50mL), and dried in a vacuum (yield 6.5g). A further quantity (1.5g) can be obtained by keeping the mother liquors and washings at -10o for 1 week. The DL-isomer has m 167-170o(dec) after recrystallisation from H2O/EtOH or MeOH. [Neuhaus & Korkes Biochemical Preparations 6 75 1958, Neuhaus & Byrne J Biol Chem 234 113 1959, IR: F.lsch & Mellander Acta Chem Scand 11 1232 1957, Beilstein 4 IV 3120.]

[1] L ERIKSEN  C T. [3H]-L-2-amino-4-phosphonobutyrate labels a metabotropic glutamate receptor, mGluR4a.[J]. British Journal of Pharmacology, 1995, 116 8: 3279-3287. DOI: 10.1111/j.1476-5381.1995.tb15136.x
[2] P J CONN  J P P. Pharmacology and functions of metabotropic glutamate receptors.[J]. Annual review of pharmacology and toxicology, 1997, 37: 205-237. DOI: 10.1146/annurev.pharmtox.37.1.205
[3] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.
[4] TRAVIS J. BAILEY. The inhibitor of phagocytosis, O-phospho-l-serine, suppresses Müller glia proliferation and cone cell regeneration in the light-damaged zebrafish retina[J]. Experimental eye research, 2010, 91 5: Pages 601-612. DOI: 10.1016/j.exer.2010.07.017
[5] JONATHAN P SAXE. A phenotypic small-molecule screen identifies an orphan ligand-receptor pair that regulates neural stem cell differentiation.[J]. Chemistry & biology, 2007, 14 9: 1019-1030. DOI: 10.1016/j.chembiol.2007.07.016