O-Phospho-L-serine

Modify Date: 2025-08-25 18:22:54

O-Phospho-L-serine Structure
O-Phospho-L-serine structure
 Common Name O-Phospho-L-serine
CAS Number 407-41-0 Molecular Weight 185.072
Density 1.8±0.1 g/cm3 Boiling Point 475.4±55.0 °C at 760 mmHg
Molecular Formula C3H8NO6P Melting Point 190 °C(lit.)
MSDS Chinese USA Flash Point 241.3±31.5 °C

 Use of O-Phospho-L-serine


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.

 Names

Name O-phospho-L-serine
Synonym More Synonyms

 O-Phospho-L-serine 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
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.

 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

 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

Fmoc-O-(benzylphospho)-L-serine structure

Fmoc-O-(benzylp...

CAS#:158171-14-3

~60%

O-Phospho-L-serine Structure

O-Phospho-L-serine

CAS#:407-41-0

Literature: US2013/29920 A1, ; Paragraph 0700 ;
(S)-3-amino-2-oxetanone trifluoroacetic acid salt structure

(S)-3-amino-2-o...

CAS#:112839-94-8

~87%

O-Phospho-L-serine Structure

O-Phospho-L-serine

CAS#:407-41-0

Literature: Journal of the American Chemical Society, , vol. 110, p. 2237
L-serine structure

L-serine

CAS#:56-45-1

~%

O-Phospho-L-serine Structure

O-Phospho-L-serine

CAS#:407-41-0

Literature: Bioorganic Chemistry, , vol. 38, # 2 p. 74 - 80
DL-O-Phosphoserine structure

DL-O-Phosphoserine

CAS#:17885-08-4

~%

O-Phospho-L-serine Structure

O-Phospho-L-serine

CAS#:407-41-0

Literature: Journal of Biological Chemistry, , vol. 106, p. 595,599
N/A structure

N/A

CAS#:3695-66-7

~%

O-Phospho-L-serine Structure

O-Phospho-L-serine

CAS#:407-41-0

Literature: Journal of Biochemistry (Tokyo, Japan), , vol. 29, p. 292,299
DL-O-Phosphoserine structure

DL-O-Phosphoserine

CAS#:17885-08-4

~%

D-serine structure

D-serine

CAS#:312-84-5

L-serine structure

L-serine

CAS#:56-45-1

O-Phospho-L-serine Structure

O-Phospho-L-serine

CAS#:407-41-0

Detail
Literature: Advanced Synthesis and Catalysis, , vol. 349, # 8-9 p. 1349 - 1352
N-benzyloxycarbonyl-O-diphenoxyphosphoryl-L-serine benzyl ester structure

N-benzyloxycarb...

CAS#:1195249-63-8

~%

O-Phospho-L-serine Structure

O-Phospho-L-serine

CAS#:407-41-0

Literature: Acta Chemica Scandinavica (1947-1973), , vol. 11, p. 1232,1235

 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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 Synonyms

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
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