Synthesis of new β- and γ-benzyloxy-S-glutamic acid derivatives and evaluation of their activity as inhibitors of excitatory amino acid transporters

Lucia Tamborini, Paola Conti, Andrea Pinto, Simona Colleoni, Marco Gobbi, Carlo De Micheli

Research output: Contribution to journalArticlepeer-review

Abstract

An efficient stereoselective preparation of the two enantiomerically pure diasteroisomers of γ-benzyloxy-S-glutamic acid was performed using trans-4-hydroxy-l-proline as a source of chirality, while the erythro and threo isomers of β-benzyloxy-S-glutamic acid were prepared starting from (R)-Garner's aldehyde. All new derivatives were tested for their inhibitory activity against excitatory amino acid transporters in a rat synaptosomal preparation and their IC50 values were compared to that of TBOA, a one carbon lower homologue commonly used as the reference blocker of glutamate transporters.

Original languageEnglish
Pages (from-to)6083-6089
Number of pages7
JournalTetrahedron
Volume65
Issue number31
DOIs
Publication statusPublished - Aug 1 2009

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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