Synthesis of four diastereomeric L-2-(carboxycyclopropyl)glycines. Conformationally constrained L-glutamate analogs

Stereoselective Formal Synthesis of (+)-Allokainic Acid <i>via</i> Thiol-Mediated Acyl Radical Cyclization

“…38,39) N-Alkylation of 7 was successful when potassium tert-butoxide was used as a base with 18-crown-6 to give 8 in 87% yield. 38) For the deprotonation of 7, it was important to add a pre-mixed solution of the alkoxide and the crown ether to a solution of 7 cooled in an ice-water bath before the addition of the bromide.…”

Elucidation of Excitatory Neurotransmission and Membrane Protein Integration Mechanisms

“…First, we focused on conformationally constrained glutamate analogs for GluR ligands and synthesized 2-(2-carboxycyclopropyl)glycines (CCGs) (Figure 2). 5,6 We clearly demonstrated that GluRs recognize the conformation of L-Glu because the extended isomer CCG-I selectively interacted with mGluRs, whereas the folded isomer CCG-IV more potently activated iGluRs by 100-fold than did L-Glu. Interestingly, CCG-III, another folded isomer, enhanced the iGluRs responses by the co-administration of L-Glu, despite the fact that CCG-III itself activated iGluRs with lesser potency than did L-Glu.…”

“…Interestingly, CCG-III, another folded isomer, enhanced the iGluRs responses by the co-administration of L-Glu, despite the fact that CCG-III itself activated iGluRs with lesser potency than did L-Glu. 5,6 We found that the potentiation was attributed to inhibition of removal of L-Glu; that is, inhibition of glutamate transporters. At that time, studies on glutamate transporters trailed behind those of the receptors mainly because the transporters, unlike the receptors, received little attention as drug targets.…”

Development of Useful Reactions Involving Tandem Cyclizations Based on the Novel Reactivities of Allenic Compounds

“…2). 118) Moreover, heterocyclic compounds with this ring system are known as useful intermediates for cyclopropane amino acids such as conformationally restricted analogues of L-glutamate 119) and g-aminobutyric acid (GABA). 120,121) Therefore, stereoselective construction of a nonracemic 3-azabicyclo[3.1.0]hexane framework is an attractive research subject for organic chemists.…”