Synthesis and biology of the rigidified glutamate analogue, trans-2-carboxyazetidine-3-acetic acid (t-CAA)

Alan P. Kozikowski; Yi Liao; Werner Tückmantel; Shaomeng Wang; Sergey Pshenichkin; Alexander Surin; Christian Thomsen; Jarda T. Wroblewski

doi:10.1016/0960-894X(96)00464-7

Synthesis and biology of the rigidified glutamate analogue, trans-2-carboxyazetidine-3-acetic acid (t-CAA)

Alan P. Kozikowski, Yi Liao, Werner Tückmantel, Shaomeng Wang, Sergey Pshenichkin, Alexander Surin, Christian Thomsen, Jarda T. Wroblewski

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Abstract

Chemical approaches to the (-)- and (+)-trans-2-carboxyazetidine-3-acetic acids (-)-1 and (+)-1, and their homologues (-)-2 and (+)-2, compounds that represent rigidified analogues of glutamate (glu), are reported together with the complete biological characterization of (+)-1 (t-CAA) at the known glu recognition sites. t-CAA was found to be an inhibitor of Na⁺-dependent glu uptake and to act as a kainate receptor ligand.

Original language	English (US)
Pages (from-to)	2559-2564
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	6
Issue number	21
DOIs	https://doi.org/10.1016/0960-894X(96)00464-7
State	Published - Nov 5 1996
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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title = "Synthesis and biology of the rigidified glutamate analogue, trans-2-carboxyazetidine-3-acetic acid (t-CAA)",

abstract = "Chemical approaches to the (-)- and (+)-trans-2-carboxyazetidine-3-acetic acids (-)-1 and (+)-1, and their homologues (-)-2 and (+)-2, compounds that represent rigidified analogues of glutamate (glu), are reported together with the complete biological characterization of (+)-1 (t-CAA) at the known glu recognition sites. t-CAA was found to be an inhibitor of Na+-dependent glu uptake and to act as a kainate receptor ligand.",

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T1 - Synthesis and biology of the rigidified glutamate analogue, trans-2-carboxyazetidine-3-acetic acid (t-CAA)

AU - Kozikowski, Alan P.

AU - Liao, Yi

AU - Tückmantel, Werner

AU - Wang, Shaomeng

AU - Pshenichkin, Sergey

AU - Surin, Alexander

AU - Thomsen, Christian

AU - Wroblewski, Jarda T.

PY - 1996/11/5

Y1 - 1996/11/5

N2 - Chemical approaches to the (-)- and (+)-trans-2-carboxyazetidine-3-acetic acids (-)-1 and (+)-1, and their homologues (-)-2 and (+)-2, compounds that represent rigidified analogues of glutamate (glu), are reported together with the complete biological characterization of (+)-1 (t-CAA) at the known glu recognition sites. t-CAA was found to be an inhibitor of Na+-dependent glu uptake and to act as a kainate receptor ligand.

AB - Chemical approaches to the (-)- and (+)-trans-2-carboxyazetidine-3-acetic acids (-)-1 and (+)-1, and their homologues (-)-2 and (+)-2, compounds that represent rigidified analogues of glutamate (glu), are reported together with the complete biological characterization of (+)-1 (t-CAA) at the known glu recognition sites. t-CAA was found to be an inhibitor of Na+-dependent glu uptake and to act as a kainate receptor ligand.

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Synthesis and biology of the rigidified glutamate analogue, trans-2-carboxyazetidine-3-acetic acid (t-CAA)

Abstract

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