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Synthesis of [3H]2-amino-4-phosphonobutyric Acid and Characterization of Its Binding to Rat Brain Membranes: A Selective Ligand for the chloride/calcium-dependent Class of L-glutamate Binding Sites

Synthesis of [3H]2-amino-4-phosphonobutyric Acid and Characterization of Its Binding to Rat Brain Membranes: A Selective Ligand for the chloride/calcium-dependent Class of L-glutamate Binding Sites

D T Monaghan, M C McMills, A R Chamberlin, C W Cotman

Brain Res. 1983 Nov 14;278(1-2):137-44.

PMID: 6640305

Abstract:

[3H]2-amino-4-phosphonobutyric acid was synthesized by the conjugate addition of 1-lithio-2-trimethylsilyethyne to diethyl ethynylphosphate followed by catalytic tritiation and hydrolysis. Radiolabelled 2-amino-4-phosphonobutyric acid binds to a distinct class of L-glutamate binding sites and does not exhibit appreciable binding to sites not displaced by L-glutamate. The binding affinity (Kd = 5.1 +/- 0.4 microM) and pharmacological profile correspond to those values obtained from physiological studies of 2-amino-4-phosphonobutyric acid inhibition of synaptic transmission, and to those values obtained in [3H]L-glutamate binding assays. [3H]2-amino-4-phosphonobutyric acid does not exhibit significant binding to the Cl-/Ca2+-independent L-glutamate binding site(s), nor to the Na+-dependent L-glutamate binding site (up to 50 mM Na+). These data provide further evidence that the physiological action of 2-amino-4-phosphonobutyric acid is mediated by the previously described Cl-/Ca2+-dependent L-glutamate binding sites, and provides an assay system which is optimal for the study of these sites.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP20263074	(±)-2-Amino-4-phosphonobutyric acid		20263-07-4	Price

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