O-Phospho-L-serine

O-Phospho-L-serine Basic information
Product Name:O-Phospho-L-serine
Synonyms:L-O-PHOSPHOSERINE;L-SERINE-O-PHOSPHATE;L-PHOSPHOSERINE;H-SER(PO3H2)-OH;PHOSPHATIDYLETHANOLAMINE(EGG)(RG);O-Phosho-L-serine;O-Phosphorylserine;Phospho-L-serine
CAS:407-41-0
MF:C3H8NO6P
MW:185.07
EINECS:206-986-0
Product Categories:Glutamate receptor;Amino Acids;Biochemistry;Biological-modified Amino Acids
Mol File:407-41-0.mol
O-Phospho-L-serine Structure
O-Phospho-L-serine Chemical Properties
Melting point 190 °C(lit.)
alpha [α]D20 +14~+18°(c=5,dil.HCl)
Boiling point 475.4±55.0 °C(Predicted)
density 1.809±0.06 g/cm3(Predicted)
vapor pressure 0Pa at 20℃
storage temp. under inert gas
solubility H2O: 50 mg/mL hot, clear, colorless to slightly yellow
form Crystalline Powder
pkapK1:2.08;pK2:5.65;pK3:9.74 (25°C)
color White
Water Solubility 28.34g/L at 20℃
Merck 14,7363
BRN 1726826
InChIKeyBZQFBWGGLXLEPQ-UWTATZPHSA-N
CAS DataBase Reference407-41-0(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 21/22
Safety Statements 36/37
RIDADR UN 3261 8 / PGII
WGK Germany 3
10
HS Code 29225090
MSDS Information
ProviderLanguage
L-Serine monophosphoric acid English
SigmaAldrich English
O-Phospho-L-serine Usage And Synthesis
DescriptionO-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.
Chemical PropertiesWhite powder
UsesL-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.
Usesroborant
UsesO-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.
DefinitionChEBI: 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.
General DescriptionMonoclonal Anti-Phosphoserine (mouse IgG1 isotype) is derived from the hybridoma produced by the fusion of mouse myeloma cells and splenocytes from an immunized mouse.
Flammability and ExplosibilityNotclassified
Biological ActivityGroup III metabotropic glutamate receptor agonist; analog of L-AP4 (L-(+)-2-Amino-4-phosphonobutyric acid ). Inhibits proliferation and enhances neuronal differentiation in progenitor cells.
Biochem/physiol ActionsProtein 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.
storageRoom temperature
Purification MethodsRecrystallise 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.]
O-Phospho-L-serine Preparation Products And Raw materials
Preparation ProductsS-2-Hydroxyethyl-L-cysteine
BOC-O-DIBENZYLPHOSPHO-L-SERINE O-Phospho-L-serine N(ALPHA)-BOC-O-(DIMETHYLPHOSPHO)-L-THREO O-PHOSPHO-D-SERINE 1,2-DICAPRYL-SN-GLYCERO-3-[PHOSPHO-L-SERINE](SODIUM SALT) L-ALPHA-PHOSPHATIDYLSERINES, BRAIN, BOVINE 1-OLEOYL-2-HYDROXY-SN-GLYCERO-3[PHOSPHO-L-SERINE](SODIUM SALT) Ethyl 2-(Chlorosulfonyl)acetate O-PHOSPHO-L-SERINE RESIN Ascoric Acid 1,2-DIACYL-SN-GLYCERO-3-PHOSPHO-L-SERINE SODIUM SALT ROCK PHOSPHATE 1,2-DILAUROYL-SN-GLYCERO-3-PHOSPHO-L-SERINE SODIUM SALT phosphate 1-PALMITOYL-SN-GLYCERO-3-PHOSPHO-L-SERINE SODIUM SALT BOC-SER(PO3ME2)-OH BOC-O-DIPHENYLPHOSPHO-L-SERINE 1,2-DIMYRISTOYL-SN-GLYCERO-3-PHOSPHO-L-SERINE SODIUM SALT

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