A7929

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

Name: <SC>L</SC>-(+)-2-Amino-4-phosphonobutyric acid
Brand: SIGMA
Price: 96.3 CHF

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

Synonyme(s) :

L-AP-4, L-AP4

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A propos de cet article

Formule empirique (notation de Hill) :

C₄H₁₀NO₅P

Numéro CAS:

23052-81-5

Poids moléculaire :

183.10

NACRES:

NA.32

PubChem Substance ID:

24891296

UNSPSC Code:

12352106

MDL number:

MFCD00083244

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Nom du produit

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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Cet article	A1910	A6060	C8655
Sigma-Aldrich A7929 L-(+)-2-Amino-4-phosphonobutyric acid	Sigma-Aldrich A1910 (±)-2-Amino-4-phosphonobutyric acid	Sigma-Aldrich A6060 Calpain Inhibitor II	Sigma-Aldrich C8655 4-Chloro-L-phenylalanine
form powder	form solid	form powder	form powder
optical purity optical purity: ≥95% (HPLC, Marfey′s reagent)	optical purity -	optical purity -	optical purity -
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)	Gene Information human ... GRIN1(2902), GRIN2A(2903), GRIN2B(2904), GRIN2C(2905), GRIN2D(2906), GRINA(2907) rat ... Grin2b(24410)	Gene Information -	Gene Information human ... TPH1(7166), TPH2(121278) mouse ... TPH1(21990), TPH2(216343) rat ... TPH1(24848), TPH2(317675)

Biochem/physiol Actions

mGluR₄ and mGluR₆ metabotropic glutamate receptor agonist.

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

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dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number

0000215229

0000215221

0000184519

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Consulter la Bibliothèque de documents

A virtual screening hit reveals new possibilities for developing group III metabotropic glutamate receptor agonists.

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

Activity-dependent synaptic integration and modulation of bilateral excitatory inputs in an auditory coincidence detection circuit.

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

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

LRIT3 is Required for Nyctalopin Expression and Normal ON and OFF Pathway Signaling in the Retina.

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

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

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