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O-Phospho-L-serine

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O-Phospho-L-serine Basic information
O-Phospho-L-serine Chemical Properties
  • Melting point:190 °C(lit.)
  • Boiling point:475.4±55.0 °C(Predicted)
  • alpha [α]D20 +14~+18°(c=5,dil.HCl)
  • Density 1.809±0.06 g/cm3(Predicted)
  • 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
  • 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
O-Phospho-L-serine Usage And Synthesis
  • Chemical PropertiesWhite powder
  • Usesroborant
  • 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.
  • 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.
  • 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.
  • 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.]
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