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Key Documents

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A7929

Sigma-Aldrich

L-(+)-2-Amino-4-phosphonobutyric acid

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

Sinónimos:

L-AP-4, L-AP4

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About This Item

Fórmula empírica (notación de Hill):
C4H10NO5P
Número de CAS:
23052-81-5
Peso molecular:
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

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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
Shijun Weng et al.
PloS one, 8(6), e66480-e66480 (2013-06-14)
Intrinsically photosensitive retinal ganglion cells (iprgcs) are depolarized by light by two mechanisms: directly, through activation of their photopigment melanopsin; and indirectly through synaptic circuits driven by rods and cones. To learn more about the rod and cone circuits driving
Chelliah Selvam et al.
Journal of medicinal chemistry, 50(19), 4656-4664 (2007-08-29)
L-2-Amino-4-phosphonobutyric acid (l-AP4), l-2-amino-4-thiophosphonobutyric acid (l-thioAP4), and l-2-amino-4-(hydroxy)phosphinylbutyric acid (desmethylphosphinothricin, DMPT) were synthesized from protected vinylglycine. They were tested as agonists at group III metabotropic glutamate receptors (mGluR) along with phosphinothricin (PT). DMPT and PT display a much lower potency
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
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