Literature

Abstract

The first synthesis of one of the 4 possible stereoisomers of 3,4-dihydroxy-L-glutamic acid ((3S,4S)-DHGA 3), a natural product of unknown configuration, is described. The synthesis is based on the Lewis acid catalyzed reaction of benzyl alcohol with a D-ribose-derived 2,3-aziridino-gamma-lactone 4-benzyl carboxylate (6). Preliminary pharmacological studies showed that (3S,4S)-3 is an agonist of metabotropic glutamate receptors of type 1 (mGluR1) and a weak antagonist of mGluR4 but has no discernible activity with respect to mGluR2. This activity profile can be rationalized by fitting extended conformations of (3S,4S)-3 in proposed models of each of these receptor subtypes.

DOI： 10.1016/s0960-894x(99)00641-1

First enantiospecific synthesis of a 3,4-dihydroxy- l -glutamic acid [(3 S ,4 S )-DHGA], a new mGluR1 agonist

Bioorganic & Medicinal Chemistry Letters 2000.0

New 4-Functionalized Glutamate Analogues Are Selective Agonists at Metabotropic Glutamate Receptor Subtype 2 or Selective Agonists at Metabotropic Glutamate Receptor Group III

Journal of Medicinal Chemistry 2016.0

Synthesis and biological activity of glutamic acid derivatives

Bioorganic & Medicinal Chemistry Letters 1998.0

Synthesis and Pharmacological Characterization at Glutamate Receptors of the Four Enantiopure Isomers of Tricholomic Acid

Journal of Medicinal Chemistry 2008.0

α-Amino-β-fluorocyclopropanecarboxylic acids as a new tool for drug development: Synthesis of glutamic acid analogs and agonist activity towards metabotropic glutamate receptor 4

Bioorganic & Medicinal Chemistry 2012.0

(2S,1‘S,2‘R,3‘R)-2-(2‘-Carboxy-3‘-hydroxymethylcyclopropyl) Glycine Is a Highly Potent Group 2 and 3 Metabotropic Glutamate Receptor Agonist with Oral Activity