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Merck

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

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Product Name

L-(+)-2-Amino-4-phosphonobutyric acid, optical purity optical purity: ≥95% (HPLC, Marfey′s reagent)

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

SMILES string

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

InChI key

DDOQBQRIEWHWBT-VKHMYHEASA-N

form

powder

optical purity

optical purity: ≥95% (HPLC, Marfey′s reagent)

Quality Level

200

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

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000215229
0000215229
0000215221
0000215221
0000184519

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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
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
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
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
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
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