… Synthesis of (1 R, 4 S, 5 R, 6 S)-3-Azabicyclo [3.3. 0] octane-4, 6-dicarboxylic Acid A Novel Inhibitor at Human Glutamate Transporter Subtypes 1, 2, and 3

L Bunch, B Nielsen, AA Jensen…

Index: Braeuner-Osborne, Hans; Bunch, Lennart; Chopin, Nathalie; Couty, Francois; Evano, Gwilherm; Jensen, Anders A.; Kusk, Mie; Nielsen, Birgitte; Rabasso, Nicolas Organic and Biomolecular Chemistry, 2005 , vol. 3, # 21 p. 3926 - 3936

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Citation Number: 20

Abstract

The natural product kainic acid is used as template for the rational design of a novel conformationally restricted (S)-glutamic acid (Glu) analogue,(1 R, 4 S, 5 R, 6 S)-3-azabicyclo [3.3. 0] octane-4, 6-dicarboxylic acid (1a). The target structure 1a was synthesized from commercially available (S)-pyroglutaminol, in an enantioselective fashion, in 14 steps. Pharmacological characterization of 1a at human glutamate transporter subtypes 1, 2, and ...