The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: cis-4-Aminocyclohexane carboxylic acid(SMILESS: N[C@H]1CC[C@H](CC1)C(O)=O,cas:3685-23-2) is researched.Category: chiral-oxygen-ligands. The article 《Characterization of an inhibitory receptor in rat hippocampus. A microiontophoretic study using conformationally restricted amino acid analogs》 in relation to this compound, is published in British Journal of Pharmacology. Let’s take a look at the latest research on this compound (cas:3685-23-2).
The inhibitory potencies of GABA [56-12-2], β-alanine [107-95-9], and glycine [56-40-6] in rat hippocampal pyramidal cells were determined and compared with those of substituted aminocyclopentane and aminocyclohexane carboxylic acids (ACPC and ACHC resp.). The order of effectiveness of the small aliphatic amino acids was GABA > β-alanine > glycine. GABA-induced inhibition was inhibited by iontophoresis of bicuculline or picrotoxin but not strychnine-HCl. The inhibitory abilities of the substituted ACPC and ACHC derivatives was a direct function of the separation of NH2 and CO2H groups in both series of cyclic amino acids. The most potent inhibition was observed when the spatial separation was similar to that of the extended GABA mol. (4.74 Å). Inhibition by (±)-cis-3-aminocyclopentanecarboxylic acid was blocked by simultaneous application of bicuculline or picrotoxin, but not by strychnine-HCl. The physiol. active conformation of GABA is probably the fully extended mol. and one dimension of the postsynaptic receptor site is probably within the range 4.2-4.8 Å.
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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate