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A7929

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

Name: <SC>L</SC>-(+)-2-Amino-4-phosphonobutyric acid
Brand: SIGMA

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

Form:

powder

Quality level:

200

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Properties

form

powder

Quality Level

200

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)

Description

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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Synthesis and biological evaluation of 1-amino-2-phosphonomethylcyclopropanecarboxylic acids, new group III metabotropic glutamate receptor agonists.

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

Mouse ganglion-cell photoreceptors are driven by the most sensitive rod pathway and by both types of cones.

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

L-(+)-2-Amino-4-thiophosphonobutyric acid (L-thioAP4), a new potent agonist of group III metabotropic glutamate receptors: increased distal acidity affords enhanced potency.

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

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Global Trade Item Number

SKU	GTIN
A7929-1MG	04061826740934
A7929-.5MG	04061833002018