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444227

Sigma-Aldrich

O-Phospho-L-serine

97%

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
Beilstein/REAXYS Number:
1726826
EC Number:
206-986-0
MDL number:
MFCD00065935
UNSPSC Code:
12352103

assay

97%

optical activity

[α]20/D +16.0°, c = 1 in 2 M HCl

mp

190 °C (lit.)

SMILES string

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

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

InChI key

BZQFBWGGLXLEPQ-REOHCLBHSA-N

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Application

This compound is a competitive antagonist at the N-methyl-D-aspartate recognition site. It has been found in elevated levels in brain tissue of people with Alzheimer′s disease.[1] This membrane metabolite is also an antagonist of receptor-mediated hydrolyses of inositol phospholipids.[2]

Biochem/physiol Actions

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

replaced by

Product No.
Description
Pricing

P0878

O-Phospho-L-serine

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Certificates of Analysis (COA)

Lot/Batch Number
19428AB
15914AA
08105JN
04611LO
04529JA

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W E Klunk et al.
Molecular and chemical neuropathology, 15(1), 51-73 (1991-08-01)
L-Phosphoserine is a membrane metabolite that is elevated in Alzheimer's disease brain. This compound has close structural similarity to L-glutamate. Electrophysiological studies indicate that L-phosphoserine has an acute inhibitory effect, but a delayed excitatory action. A hypothesis is developed based
W E Klunk et al.
Journal of neurochemistry, 56(6), 1997-2003 (1991-06-01)
L-Phosphoserine is one of the phosphomonoesters elevated in Alzheimer's disease brain and has close structural similarity to L-glutamate. This study attempts to define precisely the actions of L-phosphoserine at L-glutamate receptor subtypes. L-Phosphoserine is shown to bind to N-methyl-D-aspartate and

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