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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 Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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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