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A7845

Sigma-Aldrich

ATPO

solid

Synonym(s):

(R,S)-2-Amino-3-[5-tert-butyl-3-(phosphonomethoxy)-4-isoxazolyl]propionic acid

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About This Item

Empirical Formula (Hill Notation):
C11H19N2O7P
CAS Number:
252930-37-3
Molecular Weight:
322.25
MDL number:
MFCD03452828
UNSPSC Code:
12352200
PubChem Substance ID:
24278239

form

solid

solubility

1 M NaOH: soluble 7 mg/mL
DMSO: insoluble
H2O: insoluble

SMILES string

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

InChI

1S/C11H19N2O7P/c1-11(2,3)8-6(4-7(12)10(14)15)9(13-20-8)19-5-21(16,17)18/h7H,4-5,12H2,1-3H3,(H,14,15)(H2,16,17,18)

InChI key

AGSOOCUNMTYPSE-UHFFFAOYSA-N

Gene Information

human ... GRIA1(2890) , GRIA2(2891) , GRIA3(2892) , GRIA4(2893)
rat ... Gria1(50592) , Grik1(29559) , Grin2a(24409)

Application

The phosphono amino acid, (RS)-2-amino-3-[5-tert-butyl-3-(phosphonomethoxy)-4-isoxazolyl+ ++]propio nic acid (ATPO) is a competitive antagonist at GluR1-4 (AMPA-preferring) receptors. ATPO is a structural hybrid between the NMDA antagonist (RS)-2-amino-7-phosphonoheptanoic acid (AP7) and the AMPA/GluR5 agonist, (RS)-2-amino-3-(5-tert-butyl-3-hydroxy-4-isoxazolyl)propionic acid (ATPA).

Biochem/physiol Actions

Competitive antagonist at GluR1-4 (AMPA-preferring) receptors.

Storage Class

13 - Non 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
051K4710

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U Madsen et al.
Journal of medicinal chemistry, 39(8), 1682-1691 (1996-04-12)
(RS)-2-Amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid (AMPA, 5) and the selective AMPA receptor antagonist (RS)-2-amino-3-[3-(carboxymethoxy)-5-methyl-4-isoxazolyl]propionic acid (AMOA, 7) have been used as leads for the design and synthesis of a number of potential AMPA receptor antagonists. Two parallel series of AMOA analogs were synthesized
Yuliia I Komisarenko et al.
Frontiers in endocrinology, 9, 600-600 (2018-10-26)
Introduction: Combined endocrine pathology is a serious healthcare problem in Ukraine. This prospective study assessed the blood levels of 25-hydroxyvitamin D [25(OH)D] and markers of immune function in response to vitamin D intervention in patients with type 1 and type
P Wahl et al.
Molecular pharmacology, 53(3), 590-596 (1998-04-04)
The activity of the (R, S)-2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid (AMPA) receptor antagonist, (R,S) -2-amino-3-[5-tert-butyl-3-(phosphonomethoxy)-4-isoxazolyl] propionic acid (ATPO), at recombinant ionotropic glutamate receptors (GluRs) was evaluated using electrophysiological techniques. Responses at homo- or heterooligomeric AMPA-preferring GluRs expressed in human embryonic kidney (HEK) 293
Ana Beatriz B A Da Costa et al.
Hemodialysis international. International Symposium on Home Hemodialysis, 20(1), 31-37 (2015-08-08)
Chronic kidney disease has been known to affect thyroid hormone metabolism. Low serum levels of T3 and T4 are the most remarkable laboratorial findings. A high incidence of goiter and nodules on thyroid ultrasonography has been reported in patients with
E H Møller et al.
Chirality, 11(10), 752-759 (1999-11-24)
The phosphono amino acid, (RS)-2-amino-3-[5-tert-butyl-3-(phosphonomethoxy)-4-isoxazolyl+ ++]propio nic acid (ATPO), is a structural hybrid between the NMDA antagonist (RS)-2-amino-7-phosphonoheptanoic acid (AP7) and the AMPA and GluR5 agonist, (RS)-2-amino-3-(5-tert-butyl-3-hydroxy-4-isoxazolyl)propionic acid (ATPA). ATPO has been resolved into (S)-ATPO and (R)-ATPO using chiral HPLC
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