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A7929

Sigma-Aldrich

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:
23052-81-5
Molecular Weight:
183.10
MDL number:
MFCD00083244
UNSPSC Code:
12352106
PubChem Substance ID:
24891296
NACRES:
NA.32

form

powder

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)

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Biochem/physiol Actions

mGluR4 and mGluR6 metabotropic glutamate receptor agonist.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
Yong Lu et al.
The Journal of physiology, 596(10), 1981-1997 (2018-03-25)
Binaural excitatory inputs to coincidence detection neurons in nucleus laminaris (NL) play essential roles in interaural time difference coding for sound localization. Here, we show that the two excitatory inputs are physiologically nearly completely segregated. Synaptic integration shows linear summation
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
Dao-Qi Zhang et al.
PloS one, 7(8), e42647-e42647 (2012-08-11)
The canonical flow of visual signals proceeds from outer to inner retina (photoreceptors → bipolar cells → ganglion cells). However, melanopsin-expressing ganglion cells are photosensitive and functional sustained light signaling to retinal dopaminergic interneurons persists in the absence of rods
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