Chemical Properties
White solid
Uses
(+)-Nipecotic acid ((+)-β-Homoproline) is a GABA transport inhibitor with potential antidepressant and anxiolytic activities. (+)-Nipecotic acid can increase the concentration of GABA in the synaptic cleft, thereby enhancing inhibitory neurotransmission. The research on (+)-Nipecotic acid provides a possible direction for the development of new inhibitory compounds for psychiatric diseases[1].
Definition
ChEBI: (S)-nipecotic acid is the (S)-enantiomer of nipecotic acid. It is an enantiomer of a (R)-nipecotic acid.
General Description
(
S)-(-)-3-Piperidinecarboxylic acid is an inhibitor of GABA (γ-aminobutyric acid) uptake.
Synthesis
(S)-piperidine-3-carboxamide and 3-piperidinecarboxylic acid were synthesized from 3-piperidinecarboxamide by the following steps:
Example 3: R-enantioselective hydrolysis of racemic 3-piperidinecarboxamide in Cupriavidus sp. strain KNK-J915 (FERM BP-10739)
1. Prepare a bacterial cell suspension by culturing strain KNK-J915 as in Example 1.
2. 0.1 ml of bacterial cell suspension was mixed with 100 mM phosphate buffer (0.1 ml, pH 7.0) containing 1.0-5.0% racemic 3-piperidine carboxamide.
3. The reaction was carried out by shaking the mixture at 30°C for 35 hours.
4. After completion of the reaction, solids such as bacterial cells were removed by centrifugation.
5. The substrate and products in the reaction mixture were derivatized by reaction with benzyl chlorocarbonate.
6. The resulting derivatives were analyzed by high performance liquid chromatography (HPLC) to determine the conversion (%) and optical purity (ee%). The results were recorded in Table 3.
HPLC analysis conditions:
- Conversion rate analysis:
- Chromatographic column: YMC-A303 (4.6 mm × 250 mm, manufactured by YMC Inc.)
- Eluent: 20 mM aqueous phosphoric acid (pH 2.5)/acetonitrile = 7/3
- Flow rate: 1.0 ml/min
- Column temperature: 35°C
- Detection wavelength: 210 nm
- Optical purity analysis:
- Chromatographic column: CHIRALPAK AD-RH (4.6 mm × 150 mm, manufactured by Daicel Chemical Industries, Ltd.)
- Elution: 20 mM phosphate buffer (pH 2.5)/acetonitrile = 7/3
- Flow rate: 0.5 ml/min
- Column temperature: room temperature
- Detection wavelength: 210 nm
References
[1] Inhibition of the uptake of GABA and related amino acids in rat brain slices by the optical isomers of nipecotic acid
