The (Z) and (E) pairs of 5-aminopent-2-enoic acid and 5-aminopent-3- enoic acid, as well as the related 5-aminopent-3-ynoic acid, have been prepared for structure-activity studies on GABA receptors. Only the (Z) isomers were active as GABA agonists with (Z)-5-aminopent-2-enoic acid being two- to four-fold more active than 5-aminopentanoic acid.
Trianions can be formed from dicarboxylic acids which contain a β,γ -double bond, and amination with chloramine yields β,γ-unsaturated α-amino acids. This methodology provides a convenient synthesis of amino acids that are inaccessible by other routes. (Z)-3-Phenylthiopent-2-enedioic acid and all four stable unsaturated analogues of the conformationally restricted glutamate analogue 1-aminocyclopentane-1,3-dicarboxylic acid have been synthesized to demonstrate the applicability of the method. The structure of one of the amino acid products, (�)-cis-1-aminocyclopent-4-ene-1,3-dicarboxylic acid (7), has been determined; it crystallizes in the space group P21/c, a 9.245(24), b 8.455(2), c 9.311(3) Ǻ, β 95.00(2)°, and the structure was refined to R 0.035 for 980 F.
Diels-Alder cycloadditions involving furans and maleimides are extensively used in organic chemistry and materials synthesis. Given the promising advances of organoruthenium complexes in therapy, we explored the possibility of exploiting...
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