Synthesis of analogues of GABA. VI. Stereoisomers of cis-3-Aminocyclohexanecarboxylic acid
- 1 January 1981
- journal article
- research article
- Published by CSIRO Publishing in Australian Journal of Chemistry
- Vol. 34 (10) , 2231-2236
- https://doi.org/10.1071/ch9812231
Abstract
The syntheses are described of (1R,3S)- and (1S,3R)-3-aminocyclohexanecarboxylic acids via unsaturated intermediates suitable for tritium labelling. The absolute stereochemistry was determined by an alternative synthesis of the (1R,3S) isomer from (R)-3-oxocyclohexanecarboxylic acid. The (1S,3R) isomer showed a similar potency to GABA as an inhibitor of the uptake of radioactive GABA by rat brain slices whereas the (1R,3S) isomer was at least 20 times less potent.Keywords
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