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A263

Sigma-Aldrich

ATPA

solid

Synonym(s):

(RS)-2-Amino-3-(3-hydroxy-5-tert-butylisoxazol-4-yl)propanoic acid

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About This Item

Empirical Formula (Hill Notation):
C10H16N2O4
CAS Number:
83654-14-2
Molecular Weight:
228.25
MDL number:
MFCD01860864
UNSPSC Code:
12352202
PubChem Substance ID:
24277951
NACRES:
NA.77

form

solid

Quality Level

100

color

white

solubility

DMSO: 10 mg/mL
H2O: 2.5 mg/mL

SMILES string

CC(C)(C)c1onc(O)c1CC(N)C(O)=O

InChI

1S/C10H16N2O4/c1-10(2,3)7-5(8(13)12-16-7)4-6(11)9(14)15/h6H,4,11H2,1-3H3,(H,12,13)(H,14,15)

InChI key

PIXJURSCCVBKRF-UHFFFAOYSA-N

Gene Information

human ... GRIK1(2897)
rat ... Gria1(50592) , Grik1(29559) , Grin2a(24409)

Biochem/physiol Actions

Selective kainate receptor agonist.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ0867
MKCM8001
MKCK5318
MKBQ2887V
040M1167

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S E Lauri et al.
Neuropharmacology, 41(8), 907-915 (2001-12-19)
The development of GluR5-selective kainate receptor ligands is helping to elucidate the functions of kainate receptors in the CNS. Here we have further characterised the actions of a GluR5 selective agonist, ATPA, and a GluR5 selective antagonist, LY382884, in the
Xiaoye Liu et al.
Frontiers in cell and developmental biology, 8, 590-590 (2020-08-01)
Migration of neutrophils across endothelial barriers to capture and eliminate bacteria is served as the first line of innate immunity. Bacterial virulence factors damage endothelium to produce inflammatory cytokines interacts with neutrophils. However, the mechanisms that behind endothelial-neutrophil interaction impact
Mai Marie Nielsen et al.
Molecular pharmacology, 63(1), 19-25 (2002-12-19)
Only a few agonists exhibit selectivity between the AMPA and the kainate subtypes of the glutamate receptor. The most commonly used kainate receptor preferring agonist, (S)-2-amino-3-(5-tert-butyl-3-hydroxy-4-isoxazolyl)propionic acid [(S)-ATPA], is an (R,S)-2-amino-3-(5-methyl-3-hydroxy-4-isoxazolyl)propionic acid (AMPA) derivative in which the methyl group at
V R J Clarke et al.
Neuropharmacology, 42(7), 889-902 (2002-06-19)
Kainate receptors are involved in a variety of synaptic functions in the CNS including the regulation of excitatory synaptic transmission. Previously we described the depressant action of the GLU(K5) selective agonist (RS)-2-amino-3-(3-hydroxy-5-tert-butylisoxazol-4-yl)propanoic acid (ATPA) on synaptic transmission in the Schaffer
Marie-Louise Lunn et al.
Journal of medicinal chemistry, 46(5), 872-875 (2003-02-21)
Two X-ray structures of the GluR2 ligand-binding core in complex with (S)-2-amino-3-(5-tert-butyl-3-hydroxy-4-isoxazolyl)propionic acid ((S)-ATPA) have been determined with and without Zn(2+) ions. (S)-ATPA induces a domain closure of ca. 21 degrees compared to the apo form. The tert-butyl moiety of
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