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P0878

Sigma-Aldrich

O-Phospho-L-serine

≥98% (TLC), powder, glutamate synthase (ferredoxin)] inhibitor

Synonym(s):

L-2-Amino-3-hydroxypropanoic acid 3-phosphate, L-SOP, L-Serine O-phosphate

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About This Item

Linear Formula:
(HO)2P(O)OCH2CH(NH2)CO2H
CAS Number:
407-41-0
Molecular Weight:
185.07
Beilstein:
1726826
EC Number:
206-986-0
MDL number:
MFCD00065935
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24277998
NACRES:
NA.32

product name

O-Phospho-L-serine,

form

powder

Quality Level

200

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

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

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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
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Detection of amino acid and peptide phosphate protonation using Raman spectroscopy
Xie Y, et al.
Analytical Biochemistry, 343(2), 223-230 (2005)
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)
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)
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)
Carlo Chiarla et al.
SpringerPlus, 3, 279-279 (2014-08-01)
The determination of plasma phosphoserine concentration in sepsis is uncommon, and the clinical and metabolic correlations of abnormally high phosphoserine are basically unknown. We analyzed 430 determinations of phosphoserine, other amino acid (AA) levels and ancillary variables obtained in 18
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