Glutamate analogs

Glucose oxidase, as protein-based redox probe, 1, 909 Glutamate analogs, lead triacetate arylation, 9, 391 Glutarates, via tin hydride-promoted radical coupling,... 

Figure 3.8 Increasing structural complexity of glutamate analogs.

AMPA Insult-(a-amino 3-()I I-5-m< thylisoxazole-4 propionate, I a potent and selective glutamate analog)... 

Glutamic and aspartic acids, which are viewed as excitatory neurotransmitter amino acids, are present in the CNS in relatively large amounts. Kainic acid, which is viewed as a rigid and therefore conformationally restricted glutamate analog, has been proposed as an agonist of it, if not as a direct receptor activator, then by sensitizing these receptors to glu by some allosteric interaction. 

In a synthetic approach to artificial glutamate analogs, a domino ROM/RCM/CM reaction of oxanorbornene 50 with vinyl acetate as the co-olefin was studied (Scheme 2.20) [13d,e]. Using only 0.5mol% of the phosphine-free catalyst 4, the tricyclic product 51 was generated quantitatively and with complete control over the geometry of the exocyclic olefin. 

Treatment of 3,4-didehydro-L-pyroglutamate, protected as a cyclic orthoester, with ESTA gave a mixture of two diastereomeric products that differed in configuration at the a-ethyl ester position (eq 11). These diastereomers could be separated and converted to enantiomeiically pure, cyclopropane L-glutamate analogs, ... 

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