A new direct synthesis of ACPA and novel AMPA analogues

David J. Burkhart; Brendan Twamley; Nicholas R. Natale

doi:10.1016/S0040-4039(01)01796-8

A new direct synthesis of ACPA and novel AMPA analogues

David J. Burkhart, Brendan Twamley, Nicholas R. Natale

University of Idaho

Research output: Contribution to journal › Article › peer-review

17 Scopus citations

Abstract

A novel synthesis of the potent glutamate neurotransmitter agonist (RS)-2-amino-3-(3-carboxy-5-methyl-4-isoxazolyl) propionic acid (ACPA) provides access to numerous analogues as drug candidates for neurological disorders. The one-pot synthesis of an alpha amino phosphonate from aldehyde 4 was successful using ErCl₃ as a catalyst. Molecular modeling of the new amino phosphonic acid with the (RS)-2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl) propionic acid (AMPA) receptor crystal structure suggests this should be an effective receptor binder.

Original language	English
Pages (from-to)	8415-8418
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	48
DOIs	https://doi.org/10.1016/S0040-4039(01)01796-8
State	Published - Nov 26 2001

Keywords

AMPA
Glutamate
Isoxazole

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10.1016/S0040-4039(01)01796-8

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title = "A new direct synthesis of ACPA and novel AMPA analogues",

abstract = "A novel synthesis of the potent glutamate neurotransmitter agonist (RS)-2-amino-3-(3-carboxy-5-methyl-4-isoxazolyl) propionic acid (ACPA) provides access to numerous analogues as drug candidates for neurological disorders. The one-pot synthesis of an alpha amino phosphonate from aldehyde 4 was successful using ErCl3 as a catalyst. Molecular modeling of the new amino phosphonic acid with the (RS)-2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl) propionic acid (AMPA) receptor crystal structure suggests this should be an effective receptor binder.",

keywords = "AMPA, Glutamate, Isoxazole",

author = "Burkhart, {David J.} and Brendan Twamley and Natale, {Nicholas R.}",

note = "Funding Information: Financial support of this research from the National Institute of Neurological Disorders and Stroke (Grant NS38444-01) is gratefully acknowledged. We thank Dr. Gary Knerr, Dr. Alex Blumenfeld, and Dr. Andrzej Paszczysnki for their spectroscopic contributions. We acknowledge Dr. Eric Gouaux for helpful discussions concerning the AMPA receptor ligand binding domain.",

year = "2001",

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doi = "10.1016/S0040-4039(01)01796-8",

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T1 - A new direct synthesis of ACPA and novel AMPA analogues

AU - Burkhart, David J.

AU - Twamley, Brendan

AU - Natale, Nicholas R.

N1 - Funding Information: Financial support of this research from the National Institute of Neurological Disorders and Stroke (Grant NS38444-01) is gratefully acknowledged. We thank Dr. Gary Knerr, Dr. Alex Blumenfeld, and Dr. Andrzej Paszczysnki for their spectroscopic contributions. We acknowledge Dr. Eric Gouaux for helpful discussions concerning the AMPA receptor ligand binding domain.

PY - 2001/11/26

Y1 - 2001/11/26

N2 - A novel synthesis of the potent glutamate neurotransmitter agonist (RS)-2-amino-3-(3-carboxy-5-methyl-4-isoxazolyl) propionic acid (ACPA) provides access to numerous analogues as drug candidates for neurological disorders. The one-pot synthesis of an alpha amino phosphonate from aldehyde 4 was successful using ErCl3 as a catalyst. Molecular modeling of the new amino phosphonic acid with the (RS)-2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl) propionic acid (AMPA) receptor crystal structure suggests this should be an effective receptor binder.

AB - A novel synthesis of the potent glutamate neurotransmitter agonist (RS)-2-amino-3-(3-carboxy-5-methyl-4-isoxazolyl) propionic acid (ACPA) provides access to numerous analogues as drug candidates for neurological disorders. The one-pot synthesis of an alpha amino phosphonate from aldehyde 4 was successful using ErCl3 as a catalyst. Molecular modeling of the new amino phosphonic acid with the (RS)-2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl) propionic acid (AMPA) receptor crystal structure suggests this should be an effective receptor binder.

KW - AMPA

KW - Glutamate

KW - Isoxazole

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U2 - 10.1016/S0040-4039(01)01796-8

DO - 10.1016/S0040-4039(01)01796-8

M3 - Article

AN - SCOPUS:0035955826

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SP - 8415

EP - 8418

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 48

ER -

A new direct synthesis of ACPA and novel AMPA analogues

Abstract

Keywords

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