1. Materials information

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	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.

 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

O-Phospho-L-serine MSDS(Chinese)

 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

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Fmoc-O-(benzylp... CAS#:158171-14-3 ~60% O-Phospho-L-serine CAS#:407-41-0

Literature: US2013/29920 A1, ; Paragraph 0700 ;

(S)-3-amino-2-o... CAS#:112839-94-8 ~87% O-Phospho-L-serine CAS#:407-41-0

Literature: Journal of the American Chemical Society, , vol. 110, p. 2237

L-serine CAS#:56-45-1 ~% O-Phospho-L-serine CAS#:407-41-0

Literature: Bioorganic Chemistry, , vol. 38, # 2 p. 74 - 80

 Precursor & DownStream

Precursor  4
CAS#:158171-14-3 Fmoc-O-(benzylp...  CAS#:112839-94-8 (S)-3-amino-2-o...  CAS#:56-45-1 L-serine  CAS#:17885-08-4 DL-O-Phosphoserine
DownStream  1
CAS#:56-45-1 L-serine

 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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