A7929
L-(+)-2-Amino-4-phosphonobutyric acid
optical purity optical purity: ≥95% (HPLC, Marfey′s reagent)
Synonym(s):
L-AP-4, L-AP4
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About This Item
Empirical Formula (Hill Notation):
C4H10NO5P
CAS Number:
Molecular Weight:
183.10
NACRES:
NA.32
PubChem Substance ID:
UNSPSC Code:
12352106
MDL number:
Form:
powder
Quality level:
form
powder
Quality Level
optical purity
optical purity: ≥95% (HPLC, Marfey′s reagent)
SMILES string
N[C@@H](CCP(O)(O)=O)C(O)=O
InChI
1S/C4H10NO5P/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H2,8,9,10)/t3-/m0/s1
InChI key
DDOQBQRIEWHWBT-VKHMYHEASA-N
Gene Information
human ... GRM1(2911), GRM2(2912), GRM3(2913), GRM4(2914), GRM6(2916), GRM7(2917), GRM8(2918)
rat ... Grm1(24414), Grm2(24415), Grm4(24417), Grm5(24418), Grm6(24419), Grm7(81672)
Biochem/physiol Actions
mGluR4 and mGluR6 metabotropic glutamate receptor agonist.
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Storage Class
11 - Combustible Solids
wgk
WGK 3
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Nazarul Hasan et al.
eNeuro, 7(1) (2020-01-22)
The first retinal synapse, photoreceptor→bipolar cell (BC), is both anatomically and functionally complex. Within the same synaptic region, a change in presynaptic glutamate release is sensed by both ON BCs (DBCs) via the metabotropic glutamate receptor 6 (mGluR6), and OFF
Pauline Sibille et al.
Journal of medicinal chemistry, 50(15), 3585-3595 (2007-07-03)
Stereoisomers of 1-amino-2-phosphonomethylcyclopropanecarboxylic acid (APCPr), conformationally restricted analogues of L-AP4 (2-amino-4-phosphonobutyric acid), have been prepared and evaluated at recombinant group III metabotropic glutamate receptors. They activate these receptors over a broad range of potencies. The most potent isomer (1S,2R)-APCPr displays
Chelliah Selvam et al.
Journal of medicinal chemistry, 53(7), 2797-2813 (2010-03-12)
(R)-PCEP (3-amino-3-carboxypropyl-2'-carboxyethyl phosphinic acid, 1), a new metabotropic glutamate receptor 4 (mGlu4R) agonist, was discovered in a previously reported virtual screening. The (S)-enantiomer and a series of derivatives were synthesized and tested on recombinant mGlu4 receptors. A large number of