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.
Synthesis of new β- and γ-benzyloxy-S-glutamic acid derivatives and evaluation of their activity as inhibitors of excitatory amino acid transporters / L. Tamborini, P. Conti, A. Pinto, S. Colleoni, M. Gobbi, C. De Micheli. - In: TETRAHEDRON. - ISSN 0040-4020. - 65:31(2009 Aug 01), pp. 6083-6089. [10.1016/j.tet.2009.05.054]
Synthesis of new β- and γ-benzyloxy-S-glutamic acid derivatives and evaluation of their activity as inhibitors of excitatory amino acid transporters
L. TamboriniPrimo
;P. Conti
Secondo
;A. Pinto;C. De MicheliUltimo
2009
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.File | Dimensione | Formato | |
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