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P0878

Sigma-Aldrich

O-Phospho-L-serine

Synonym(s):
L-2-Amino-3-hydroxypropanoic acid 3-phosphate, L-SOP, L-Serine O-phosphate
Linear Formula:
(HO)2P(O)OCH2CH(NH2)CO2H
CAS Number:
Molecular Weight:
185.07
Beilstein:
1726826
EC Number:
MDL number:
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.32

form

powder

Quality Level

storage condition

under inert gas

mp

190 °C (lit.)

SMILES string

N[C@@H](COP(O)(O)=O)C(O)=O

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

InChI key

BZQFBWGGLXLEPQ-REOHCLBHSA-N

Gene Information

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This Item
72983P5660P7769
O-Phospho-L-serine

Sigma-Aldrich

P0878

O-Phospho-L-serine

O-Phospho-L-serine certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland

Supelco

72983

O-Phospho-L-serine

storage condition

under inert gas

storage condition

-

storage condition

-

storage condition

-

mp

190 °C (lit.)

mp

190 °C (lit.)

mp

-

mp

-

Gene Information

human ... GRM4(2914), GRM7(2917), GRM8(2918)

Gene Information

-

Gene Information

-

Gene Information

-

Application

O-Phospho-L-serine has been used:
  • for the expression, purification and phosphorylation of protein
  • to study its chemical shift
  • to spectroscopically determine its pKa values using Raman spectroscopy

Biochem/physiol Actions

O-Phospho-L-serine (L-SOP) is a molecule which resembles phosphatidylserine head group and it mediates partial inhibition of microglial phagocytosis of apoptotic cells. In zebrafish, L-SOP inhibits Müller glia proliferation and blocks cone cell regeneration in the light-damaged retina. In vivo, L-SOP acts as a substrate for CysM, a cysteine synthase from Mycobacterium tuberculosis.
Group III metabotropic glutamate receptor agonist (mGluR4, mGluR7, and mGluR8).

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible, corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Customers Also Viewed

Slide 1 of 3

1 of 3

Detection of amino acid and peptide phosphate protonation using Raman spectroscopy
Xie Y, et al.
Analytical Biochemistry, 343(2), 223-230 (2005)
O-phospho-L-serine and the thiocarboxylated sulfur carrier protein CysO-COSH are substrates for CysM, a cysteine synthase from Mycobacterium tuberculosis.
O'Leary SE
Biochemistry, 47(44), 11606-11615 (2008)
Phosphorylation of OPTN by TBK1 enhances its binding to Ub chains and promotes selective autophagy of damaged mitochondria
Richter B, et al.
Proceedings of the National Academy of Sciences of the USA, 113(15), 4039-4044 (2016)
The inhibitor of phagocytosis, O-phospho-L-serine, suppresses Muller glia proliferation and cone cell regeneration in the light-damaged zebrafish retina.
Bailey TJ
Experimental Eye Research, 91(5), 601-612 (2010)
Improved peak identification in 31P-NMR spectra of environmental samples with a standardized method and peak library
Cade-Menun BJ
Geoderma, 257, 102-114 (2015)

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