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Merck
CN

79715

O-Phospho-L-serine

~95% (TLC)

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
EC Number:
206-986-0
UNSPSC Code:
12352200
PubChem Substance ID:
329768571
Beilstein/REAXYS Number:
1726826
MDL number:
MFCD00065935

Key Documents

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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

assay

~95% (TLC)

impurities

≤2% water

mp

190 °C (lit.)

solubility

H2O: 50 mg/mL, clear, colorless to slightly yellow (hot)

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Biochem/physiol Actions

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

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8B - Non-combustible corrosive hazardous materials

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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J N Verma et al.
Journal of lipid research, 26(5), 610-616 (1985-05-01)
Phosphatidylserine decarboxylase activity has been characterized in membrane preparations from Clostridium butyricum ATCC 19398. A particulate fraction was shown to catalyze the formation of phosphatidylethanolamine and plasmenylethanolamine when vesicles containing phosphatidylserine and plasmenylserine were used as substrate. No plasmenylethanolamine was
Geneviève Desjardins et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(30), 11019-11024 (2014-07-16)
The E26 transformation-specific (Ets-1) transcription factor is autoinhibited by a conformationally disordered serine-rich region (SRR) that transiently interacts with its DNA-binding ETS domain. In response to calcium signaling, autoinhibition is reinforced by calmodulin-dependent kinase II phosphorylation of serines within the
R P Hulse et al.
Neurobiology of disease, 71, 245-259 (2014-08-26)
Vascular endothelial growth factor-A (VEGF-A) is best known as a key regulator of the formation of new blood vessels. Neutralization of VEGF-A with anti-VEGF therapy e.g. bevacizumab, can be painful, and this is hypothesized to result from a loss of
Latha Ramalingam et al.
Diabetologia, 57(7), 1476-1484 (2014-04-08)
Insulin secretion from pancreatic beta cells and insulin-stimulated glucose uptake into skeletal muscle are processes regulated by similar isoforms of the soluble N-ethylmaleimide-sensitive factor-attachment protein receptor (SNARE) and mammalian homologue of unc-18 (Munc18) protein families. Double C2 domain β (Doc2b)
S A Kang-Yoon et al.
The American journal of clinical nutrition, 55(4), 865-872 (1992-04-01)
Pyridoxal 5'-phosphate (PLP) is a coenzyme in many metabolic transformations of amino acids and may play a role in their absorption and transport. This investigation analyzed the effects of large oral doses (27 mg/d) of pyridoxine (PN)-HCl over 2 wk
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