| 초록 |
L-Glutamate is the major excitatory neurotransmitter in the mammalian central nervous system and excitatory amino acid transporters (EAATs) are responsible to control the uptake of glutamate from the synaptic cleft. Aspartate derivatives have been considered as an important class of inhibitors of EAATs. Especially threo-3-benzyloxy aspartate (TBOA) is one of the widely studied non-transportable blocker for L-glutamate transporter. Since one of the enantiomers have showed more potent inhibitory properties, we have focused on the development of procedures to L-TBOA selectively from the commercially available amino acid, D-serine. In this study, high stereoselectivity (more than 20:1) has been achieved from the tandem reactions with N-hydroxymethyl protected α-amino aldehyde. After introducing α-hydroxy moiety to the aldehyde, simple treatments for the functionalization of the side chain and O-benzyl protection presented L-TBOA as a single stereoisomer. |
