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Merck

P0878

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
NACRES:
NA.32
PubChem Substance ID:
24277998
eCl@ss:
32160406
UNSPSC Code:
12352209
EC Number:
206-986-0
MDL number:
MFCD00065935
Beilstein/REAXYS Number:
1726826
Form:
powder
Quality level:
200
Storage condition:
under inert gas

Key Documents

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Product Name

O-Phospho-L-serine,

InChI key

BZQFBWGGLXLEPQ-REOHCLBHSA-N

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

SMILES string

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

form

powder

storage condition

under inert gas

mp

190 °C (lit.)

Quality Level

200

Gene Information

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

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Related Categories

Biochem/physiol Actions

Group III metabotropic glutamate receptor agonist (mGluR4, mGluR7, and mGluR8).
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.

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

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

P0878-5G: + P0878-VAR: + P0878-1G: + P0878-10MG: + P0878-BULK: + P0878-25G: + P0878-100G:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM1313
BCCK0889
BCCG8818
BCCF9576
BCCF1357

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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)
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)
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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