O-Phospho-L-serine

Names

[ CAS No. ]:
407-41-0

[ Name ]:
O-Phospho-L-serine

[Synonym ]:
dexfosfoserine
O-Phospho-L-serine
3-O-(phospho)-L-serine
P-serine
L-O-phosphoserinate
DL-SERINE PHOSPHATE HYDRATE
O-Phosphoserine
O-phosphoryl-L-serine
L-(+)-phosphoserine
O-Phosphono-L-serine
Seriphos
P-ser
L-serine-O-phosphate
3-P-SERINE
L-O-(RG)
L-Serine Phosphate
L-O-serine phosphate
L-Serine, O-phosphono-
L-O-Phosphoserine
EINECS 206-986-0
L-SOP
H-SER(P)-OH
Fosforina
MFCD00065935
Phosphoserine

Biological Activity

[Description]:

O-Phospho-L-serine is the immediate precursor to L-serine in the serine synthesis pathway, and an agonist at the group III mGluR receptors (mGluR4, mGluR6, mGluR7, and mGluR8); O-Phospho-L-serine also acts as a weak antagonist for mGluR1 and a potent antagonist for mGluR2.

[Related Catalog]:

Research Areas >> Neurological Disease

Natural Products >> Others

[Target]

Human Endogenous Metabolite

[In Vitro]

O-Phospho-L-serine (l-SOP) weakly binds to mGluR1, and antagonizes the effects of l-glutamate. l-SOP activates the group III receptors (mGluR4, mGluR6, mGluR7, and mGluR8), but mGluR7 has much lower affinity for l-SOP than the other group III receptors and also displays lower efficacy for both ligands[1]. O-Phospho-L-serine (l-SOP) generates enhanced intracellular calcium responses in mGluR4 transfected cells. l-SOP inhibits the l-glutamate mediated mGluR1 response, with a Ki of 1 mM; l-SOP displays a substantially more potent inhibition of mGluR2 activation, with a Ki of 1 μM, three orders-of-magnitude more potent than for mGluR1. l-SOP induces membrane potential changes in HEK/TRPC4 cells transfected with mGluR4 or mGluR6. l-SOP induces TRPC4β activation mediated by Gαi/o proteins[2]. O-Phospho-L-serine (L-SOP) inhibits Müller glia proliferation, without affecting light-induced photoreceptor cell death. L-SOP disrupts Müller glia proliferation subsequent to or in parallel with the activation of ascl1a and stat3 expression in the light-damaged retina. L-SOP inhibits cone cell regeneration in the light-damaged retina[3].

[References]

[1]. Kang HJ, et al. Determinants of endogenous ligand specificity divergence among metabotropic glutamate receptors. J Biol Chem. 2015 Jan 30;290(5):2870-8.

[2]. Kang HJ, et al. Selectivity and evolutionary divergence of metabotropic glutamate receptors for endogenous ligands and G proteins coupled to phospholipase C or TRP channels. J Biol Chem. 2014 Oct 24;289(43):29961-74.

[3]. Bailey TJ, et al. The inhibitor of phagocytosis, O-phospho-L-serine, suppresses Müller glia proliferation and cone cell regeneration in the light-damaged zebrafish retina. Exp Eye Res. 2010 Nov;91(5):601-12.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
475.4±55.0 °C at 760 mmHg

[ Melting Point ]:
190 °C(lit.)

[ Molecular Formula ]:
C₃H₈NO₆P

[ Molecular Weight ]:
185.072

[ Flash Point ]:
241.3±31.5 °C

[ Exact Mass ]:
185.008926

[ PSA ]:
139.89000

[ LogP ]:
-1.86

[ Vapour Pressure ]:
0.0±2.6 mmHg at 25°C

[ Index of Refraction ]:
1.552

[ Storage condition ]:
Store at 0°C

[ Water Solubility ]:
H2O: 50 mg/mL hot, clear, colorless to slightly yellow

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
21/22

[ Safety Phrases ]:
36/37

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2931900090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2931900090

[ Summary ]:
2931900090. other organo-inorganic compounds. VAT:17.0%. Tax rebate rate:13.0%. Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward). MFN tariff:6.5%. General tariff:30.0%

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