Preparation of deuterium labelled α-amino-3-hydroxy-5-methylisoxazole-4-propionic acid (AMPA)
✍ Scribed by Jørn Lauridsen; Tage Honoré
- Publisher
- John Wiley and Sons
- Year
- 1981
- Tongue
- French
- Weight
- 209 KB
- Volume
- 18
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
Abstract
The preparation of α‐amino‐3‐hydroxy‐5‐methylisoxazole‐4‐propionic acid (AMPA) with deuterium α to the carboxylic acid group (2) and in the exocyclic methyl group (5), respectively, are described. The deuterium labelled AMPA (2) was synthesized by hydrolysis and decarboxylation of the corresponding di‐ester (1), whereas the deuterium labelled AMPA (5) was prepared via a catalytic deuteration of the bromoderivative (3).
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## Abstract In vivo and in vitro studies have shown that α‐amino‐3‐hydroxy‐5‐methylisoxazole‐4‐propionic acid (AMPA)‐receptor‐mediated excitotoxicity causes cytoskeletal damage to axons. AMPA/kainate receptors are present on oligodendrocytes and myelin, but currently there is no evidence to suggest
## Abstract The excitatory, amino acid ±2‐amino‐3‐(3‐hydroxy‐5‐methylisoxazol‐4‐yl)propionic acid hydrobromide was prepared in gram quantities in an 3.3% overall yield from methylbut 2‐ynoate. The key step was the facile preparation of methyl 3‐bromo‐5‐methylisoxazole‐4‐carboxylate.