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

✍ Scribed by Philippe Dauban; Carole de Saint-Fuscien; Francine Acher; Laurent Prézeau; Isabelle Brabet; Jean-Philippe Pin; Robert H. Dodd

Publisher: Elsevier Science
Year: 2000
Tongue: English
Weight: 186 KB
Volume: 10
Category: Article
ISSN: 0960-894X
DOI: 10.1016/s0960-894x(99)00641-1

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✦ Synopsis

AbstractÐThe ®rst synthesis of one of the 4 possible stereoisomers of 3,4-dihydroxy-l-glutamic acid ((3S,4S)-DHGA 3), a natural product of unknown con®guration, is described. The synthesis is based on the Lewis acid catalyzed reaction of benzyl alcohol with a d-ribose-derived 2,3-aziridino-g-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 pro®le can be rationalized by ®tting extended conformations of (3S,4S)-3 in proposed models of each of these receptor subtypes.

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