Synthesis of Analogues of GABA. III. All Four Stereoisomers of 3-Aminocyclopentanecarboxylic Acid and a Stereochemical Correlation with Amidinomycin
- 1 January 1979
- journal article
- research article
- Published by CSIRO Publishing in Australian Journal of Chemistry
- Vol. 32 (11) , 2517-2521
- https://doi.org/10.1071/ch9792517
Abstract
All four stereoisomers of 3-aminocyclopentanecarboxylic acid have been prepared as analogues of the inhibitory neurotransmitter GABA. The amino acid degradation product from the antibiotic amidinomycin corresponds to cis-(1R,3S)-3-aminocyclopentanecarboxylic acid and thus amidinomycin is (1R,3S)-N-(2'-amidinoethyl)-3-aminocyclopentane-1-carboxamide (10). A key reaction was the stereoselective reduction of 3-hydroxyiminocyclopentanecarboxylic acid (8) to the corresponding cis amino acid (2).Keywords
This publication has 0 references indexed in Scilit: